Dimethyl Sulfoxide → 2-(2,5-Difluorophenyl)cyclopropanecarbaldehyde

HRID 1644345ノート

反応式

HRID 1644345 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[CH:19]1[CH2:21][CH:20]1[CH2:22][OH:23].C(N(CC)CC)C>ClCCl>[F:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[CH:19]1[CH2:21][CH:20]1[CH:22]=[O:23]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 66774368(2-(2,5-Difluorophenyl)cyclopropyl)methanol2 回

生成物 1

HCID 866426152-(2,5-Difluorophenyl)cyclopropanecarbaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of oxalyl chloride (1.2 mL, 13.5 mmol) in dichloromethane at −78° C. was added dimethyl sulfoxide (1.9 mL, 27 mmol) dropwise and it was stirred at −78° C. for 30 minutes. A solution of [2-(2,5-difluorophenyl)cyclopropyl]methanol (Intermediate 69) (830 mg, 4.5 mmol) in dichloromethane was added dropwise. The reaction mixture was stirred at −78° C. for 30 minutes. Triethylamine (6.3 mL, 45 mmol) was added and the reaction mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure. Silica gel chromatography with hexanes/ethyl acetate (9:1) afforded the desired product, 546 mg (66%).

後処理

  1. stirringThe reaction mixture was stirred at −78° C. for 30 minutes
  2. stirringthe reaction mixture was stirred at room temperature for 2 hours
  3. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-375a064717c4493db34111f9c4fa9bdd
出典データセット
uspto-grants-2012_02
特許番号
US08124602B2

反応ノート

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