Formic Acid → Methyl 4-[2-carboxy-4-(4-cyanophenyl)butyl]benzoate

HRID 1913759ノート

反応式

HRID 1913759 の反応式
C(N(CC)CC)C.C(O)=O.[C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([O:43][CH3:44])=[O:42])=[CH:37][CH:36]=2)(C(OCC=C)=O)[C:22]([O:24]CC=C)=[O:23])=[CH:15][CH:14]=1)#[N:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:22]([CH:21]([CH2:20][CH2:19][C:16]1[CH:15]=[CH:14][C:13]([C:11]#[N:12])=[CH:18][CH:17]=1)[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]([O:43][CH3:44])=[O:42])=[CH:37][CH:36]=1)([OH:24])=[O:23]

参加物

7

反応物 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 57831389HCID 57831389、化合物

生成物 1

HCID 57831396Methyl 4-[2-carboxy-4-(4-cyanophenyl)butyl]benzoate収率 82.2%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
10 °C

実験手順

A solution of 41.8 ml (0.3 mol) of triethylamine and 8.6 ml (0.23 mol) of formic acid in 500 ml of dioxane is added to a solution of 43.5 g (0.09 mol) of diallyl 2-[2-(4-cyanophenyl)ethyl]-2-(4-methoxycarbonylbenzyl)malonate, 1.67 g (0.01 mol) of triphenylphosphine and 410 mg of palladium acetate in 505 ml of dioxane at room temperature. The reaction mixture is then stirred at 10° C. for 2 hours. After conversion is complete, the reaction solution is cooled and the solvent is removed in vacuo. The resulting residue is purified by flash chromatography on silica gel (mobile phase: dichloromethane/methanol 50:1). 25 g (74 mmol, 82% yield) of a colourless solid are obtained.

後処理

  1. temperaturethe reaction solution is cooled
  2. customthe solvent is removed in vacuo
  3. customThe resulting residue is purified by flash chromatography on silica gel (mobile phase: dichloromethane/methanol 50:1)

出典と根拠

ORDレコード
ord-376a5c823d3f46c5828cfadd3953d283
出典データセット
uspto-grants-2013_12
特許番号
US08609727B2

反応ノート

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