Allyl bromide → HCID 10082149、化合物

HRID 344731

反応式

HRID 344731 の反応式
[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>[C:1]([CH:9]([CH2:17][CH:16]=[CH2:15])[C:10]([O:12][CH3:13])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

参加物

5

反応物 3

HCID 7841Allyl bromide2 回HCID 1086453-Pyridinepropanoic acid, beta-oxo-, methyl esterHCID 5360545Sodium

生成物 1

HCID 10082149HCID 10082149、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
25 °C

実験手順

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 (B) as a pale yellow oil (13.8 g); NMR 2.6-2.9(2H,m), 3.7(3H,s), 4.4(1 H,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).

後処理

  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

出典と根拠

ORDレコード
ord-0d6b7cb6790c4517b8e73286d44c6c58
出典データセット
uspto-grants-1991_10
特許番号
US05053415

関連ノート

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