반응 #6530

반응 방정식

allyl bromide

Methyl 2-(nicotinoyl)acetate

sodium

Allyl bromide

→

methyl-2-nicotinoyl-4-pentenoate

용매

methanol

반응 조건

후처리

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued overnight
3. 3
   workup.STIRRINGthe mixture was stirred for 48 hours
4. 4
   농축concentrated
5. 5
   기타The residual oil was partitioned between water and ether
6. 6
   추출the aqueous layer was extracted three times with ether
7. 7
   세척The combined extracts were washed with saturated brine
8. 8
   건조dried (MgSO4)
9. 9
   농축concentrated
10. 10
    기타The residue was purified by flash column chromatography
11. 11
    세척eluting with a mixture of petroleum ether (b.p. 60°-80°) and ethyl acetate (1:1

실험 절차

Methyl 2-(nicotinoyl)acetate (17.9 g, prepared by the method of E. Wenkert el al. J. Org. Chem., 1983, 48, 5006) was added under argon to a solution of sodium metal (2.3 g) in methanol (200 ml) and the resulting mixture was stirred at 25° C. for 30 mins. Allyl bromide (12.0 g) was then added and stirring was continued overnight. A further amount (about 2 g) of allyl bromide was added, the mixture was stirred for 48 hours, and then concentrated. The residual oil was partitioned between water and ether and the aqueous layer was extracted three times with ether. The combined extracts were washed with saturated brine, dried (MgSO4) and concentrated. The residue was purified by flash column chromatography, eluting with a mixture of petroleum ether (b.p. 60°-80°) and ethyl acetate (1:1, v/v) to give methyl-2-nicotinoyl-4-pentenoate (A) as a pale yellow oil (13.8 g); NMR 2.6-2.9 (2H,m), 3.7 (3H,s), 4.4 (1H,m), 4.9-5.2 (2H,m), 5.5-6.0 (1H,m), 7.2-7.5 (1H,m), 8.1-8.3 (1H,m), 8.7-8.8 (1H,m) and 9.1-9.2 (1H,m).

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