Dimethylformamide → Benzyl 3-(4-pyridyl)-2-butenoate

HRID 11447

反応式

HRID 11447 の反応式
CN(C)C=O.[C:6]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)(=O)[CH3:7].[Br-].[CH2:16]([O:23][C:24]([CH2:26][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)C>[N:12]1[CH:13]=[CH:14][C:9]([C:6]([CH3:7])=[CH:26][C:24]([O:23][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:25])=[CH:10][CH:11]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 142824-AcetylpyridineHCID 11214019(Benzyloxycarbonylmethyl)triphenylphosphonium bromide

生成物 1

HCID 67118931Benzyl 3-(4-pyridyl)-2-butenoate収率 42.4%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
70 °C

実験手順

N,N-Dimethylformamide (33 ml) was added to a mixture of 4-acetylpyridine (2.00 g, 16.5 mmol) and (benzyloxycarbonyl)methyltriphenylphosphonium bromide (8.94 g, 18.2 mmol), and the whole was stirred under ice-cooling. Potassium carbonate (9.12 g, 66.0 mmol) was added thereto, the external temperature was raised to 70° C., and the whole was stirred overnight. The reaction mixture was diluted with diethyl ether (100 ml), and the whole was washed with water (100 ml, twice) and saturated brine (50 ml) successively. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 1.77 g (42%: mixture of E form and Z form) of benzyl 3-(4-pyridyl)-2-butenoate as a pale yellow oily matter.

後処理

  1. temperaturecooling
  2. stirringthe whole was stirred overnight
  3. washthe whole was washed with water (100 ml
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-0be49fb58b2f4f039baba09b76a48389
出典データセット
uspto-grants-2006_08
特許番号
US07098226B2

関連ノート

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