Allyl bromide → HCID 10082149, 화합물

HRID 373954

반응식

HRID 373954 반응식
[C:1]([CH2:9][C:10]([O:12][CH3:13])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[Na].[CH2:15](Br)[CH:16]=[CH2:17]>CO>[CH3:13][O:12][C:10](=[O:11])[CH:9]([C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1)[CH2:17][CH:16]=[CH2:15]

참가 물질

5

반응물 3

HCID 7841Allyl bromide2회HCID 1086453-Pyridinepropanoic acid, beta-oxo-, methyl esterHCID 5360545Sodium

생성물 1

HCID 10082149HCID 10082149, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
25 °C

실험 절차

Methyl 2-(nicotinoyl)acetate (17.9 g, prepared by the method of E Wenkert et 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).

후처리

  1. stirringstirring
  2. waitwas continued overnight
  3. stirringthe mixture was stirred for 48 hours
  4. concentrationconcentrated
  5. customThe residual oil was partitioned between water and ether
  6. extractionthe aqueous layer was extracted three times with ether
  7. washThe combined extracts were washed with saturated brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe residue was purified by flash column chromatography
  11. washeluting with a mixture of petroleum ether (b.p. 60°-80°) and ethyl acetate (1:1

출처 및 근거

ORD 기록
ord-19fcb8cd5765478a8553de024e42ed10
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05166213

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