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Organic Synteses vol 70 - Meyers A.I.

Meyers A.I. , Boecman R.K. Organic Synteses vol 70 - John Wiley & Sons, 1992. - 163 p.
ISBN 0-471-57743
Download (direct link): organicsynthesesvol701992.pdf
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Scheme
O
O
Vk 0
O
74%
0
89%
201
1. The Willard H. Dow Laboratories, Department of Chemistry, The University of Michigan, Ann Arbor, Ml 48109.
2. For various activations of zinc metal see: Erdik, E. Tetrahedron 1987, 43, 2203; for zinc activation with chlorotrimethylsilane, see: (a) Gawronski, J. K. Tetrahedron Lett. 1984, 25, 2605; (b) Picotin, G.; Miginiac, P. J. Org. Chem.
1987, 52, 4796; (c) Picotin, G.; Miginiac, P. Tetrahedron Lett. 1987, 28, 4551.
3. Martinkus, K. J.; Tann, C.-H.; Gould, S. J. Tetrahedron 1983, 39, 3493.
4. Still, W. C.; Kahn, M.; Mitra, M. J. Org. Chem. 1978, 43, 2923.
5. (a) Knöchel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390; (b) Yeh, M. C. P.; Knöchel, P.; Butler, W. M.; Berk, S. C. Tetrahedron Lett.
1988, 29, 6693; (c) Majid, T. N.; Knöchel, P. Tetrahedron Lett. 1990, 31, 4413.
6. (a) Tamaru, Y.; Ochiai, H.; Nakamura, T.; Tsubaki, K.; Yoshida, Z.-i.Tetrahedron Lett. 1985, 26, 5559; (b) Tamaru, Y.; Ochiai, H.; Nakamura, T.; Yoshida, Z.-i. Tetrahedron Lett. 1986, 27, 955; (c) Nakamura, E.; Sekiya, K.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 337; (d) Tamaru, Y.; Ochiai, H.; Nakamura, T.; Yoshida, Z.-i. Org. Synth. 1989, 67, 98.
7. Yeh, M. C. P.; Knöchel, P.; Santa, L. E. Tetrahedron Lett. 1988, 29, 3887.
8. Berk, S. C.; Knöchel, P.; Yeh, M. C. P. J. Org Chem. 1988, 53, 5789.
9. Tamaru, Y.; Ochiai, H.; Nakamura, T.; Yoshida, Z.-i. Angew. Chem. 1987, 99, 1193; Angew. Chem., Intern. Ed. Engl. 1987, 26, 1157.
10. (a) Yeh, M. C. P.; Knöchel, P. Tetrahedron Lett. 1988, 29, 2395; (b) Yeh, M. C. P.; Knöchel, P. Tetrahedron Lett. 1989, 30, 4799; (c) Tamaru, Y.; Tanigawa, H.; Yamamoto, T.; Yoshida, Z.-i. Angew. Chem. 1989, 101, 358; Angew. Chem., Intern. Ed. Engl. 1989, 28, 351; (d) Majid, T. N.; Yeh, M. C. P.; Knöchel, P. Tetrahedron Lett. 1989, 30 5069.
11. (a) Comins, D. L.; O'Connor, S. Tetrahedron Lett. 1987, 28, 1843; (b) Comins,
D. L.; Foley, M. A. Tetrahedron Lett. 1988, 29, 6711.
202
12. (a) Chen. H. G.; Hoechstetter, C.; Knöchel, P. Tetrahedron Lett. 1989, 30, 4795; (b) Jackson, R. F. W.; James, K.; Wythes, M. J.; Wood, A. J. Chem. Soc., Chem. Commun. 1989, 644.
13. Retherford, C.; Chou, T.-S.; Schelkun, R. M.; Knöchel, P. Tetrahedron Lett. 1990, 31, 1833.
14. AchyuthaRao, S.; Tucker, C. E.; Knöchel, P. submitted for publication.
15. Gaudemar, M. Bull. Soc. Chim. France 1962, 974.
Appendix Chemical Abstracts Nomenclature (Collective Index Number); (Registry Number)
(E)-2-(4-Hydroxy-6-phenyl-5-hexenyl)-1 H-isoindole-1,3(2H)-dione: 1 H-lsoindole-1,3(2H)-dione, 2-(4-hydroxy-6-phenyl-5-hexenyl)- (12); (121883-31-6) 2-(3-lodopropyl)-1 H-isoindole-1,3(2H)-dione: 1 H-lsoindole-1,3(2H)-dione, 2-(3-iodopropyl)- (9); (5457-29-4)
2-(3-Bromopropyl)-1 H-isoindole-1,3(2H)-dione: Phthalimide, N-(3-bromopropyl)- (8);
1 H-lsoindole-1,3(2H)-dione, 2-(3-bromopropyl)- (9); (5460-29-7)
Sodium iodide (8,9); (7681-82-5)
Zinc (8,9); (7440-66-6)
1,2-Dibromoethane: Ethane, 1,2-dibromo- (8,9); (106-93-4)
Chlorotrimethylsilane: Silane, chlorotrimethyl- (8,9); (75-77-4)
Lithium chloride (8,9); (7447-41-8)
Copper cyanide (8,9); (544-92-3)
Boron trifluoride etherate: Ethyl ether, compd. with boron fluoride (BF3) (1:1 ) (8); Ethane, 1,1 '-oxybis-, compd. with trifluoroborane (1:1) (9); (109-63-7) (E)-Cinnamaldehyde: Cinnamaldehyde, (E)- (8); 2-Propenal, 3-phenyl-,
(E)- (9); (14371-10-9)
203
SPIROANNELATION VIA ORGANOBIS(CUPRATES):
9,9-DIMETHYLSPIRO[4.5]DECAN-7-ONE (Spiro[4.5]decan-7-one, 9,9-dimethyl-)
(COCI)2
toluene, 60°C
B.
Et2Q, 0°C
1. CuSPh, THF -78°Cto-15°C
2.
Cl
THF, -15°C
Submitted by Paul A. Wender,1-2 Alan W. White,1 and Frank E. McDonald.2 Checked by Naoki Hirayama and Hisashi Yamamoto.
204
1. Procedure
Note: All reactions should be conducted in an efficient fume hood.
A. 3-Chloro-5,5-dimethylcyclohex-2-en-1-one (1)3 (Note 1). An oven-dried, 250-mL, one-necked, round-bottomed flask is equipped with a magnetic stirring bar and graduated addition funnel topped with a nitrogen inlet. The flask is charged with dimedone (28.1 g, 200 mmol) and toluene (100 mL) (Note 2). The suspension is stirred while oxalyl chloride (35 mL, 400 mmol) is slowly added via the addition funnel over a 10-min period (Note 3). After the addition is complete and gas evolution has subsided, the addition funnel is quickly exchanged for a reflux condenser topped with a nitrogen inlet. The mixture is then heated at 60-70°C for 30 min, or until no more suspended dimedone remains and gas evolution has ceased. (Additional oxalyl chloride may be added until dimedone has completely reacted.) The reaction is allowed to cool and concentrated by rotary evaporation at reduced pressure. The crude red oil is distilled through a short path apparatus to give 3-chloro-5,5-dimethylcyclohex-2-en-1-one (1) (29.3 g, 93% yield) as a colorless oil, bp 68-71 “C (6.0 mm) (Note 4).
B. 1,4-Dilithiobutane (2).4a>5 (All transfers are conducted under dry nitrogen; reagents are introduced into reaction vessels through rubber septa using a cannula or syringe.) An oven-dried, 1-L, three-necked, round-bottomed flask is equipped with a large magnetic stirring bar and glass beads (ca. 3-mm diameter), graduated addition funnel, stopper, and large diameter nitrogen inlet (at least 2 mm in diameter). The flask is purged with nitrogen, charged with anhydrous diethyl ether (250 mL) (Note 2), and cooled to 0°C. The stopper is removed from the flask and replaced with a conical funnel while a rapid flow of dry nitrogen is passed through the flask. Lithium wire, 1% Na (9.48 g, 1.36 mol, 4.5 eq.) (Note 5), prewashed with hexanes, is held with forceps over the funnel and cut with clean scissors into pieces no larger than 2 mm in length
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