Dimethyl Sulfoxide → 2,2-Difluoro-5-methoxy-1-pentanal hydrate

HRID 568980ノート

反応式

HRID 568980 の反応式
CS(C)=[O:3].C(Cl)(=O)C(Cl)=O.[F:11][C:12]([F:20])([CH2:15][CH2:16][CH2:17][O:18][CH3:19])[CH2:13][OH:14].C(N(CC)CC)C>ClCCl>[OH2:3].[F:11][C:12]([F:20])([CH2:15][CH2:16][CH2:17][O:18][CH3:19])[CH:13]=[O:14]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 140975992,2-Difluoro-5-methoxypentan-1-ol

生成物 1

HCID 201494532,2-Difluoro-5-methoxy-1-pentanal hydrate収率 53.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒4 回

反応条件

温度
-60 °C

実験手順

A solution of dry dimethylsulfoxide (3 g, 38 mmoles) in dry dichloromethane (15 ml) is slowly added to a solution of oxalyl chloride (2.4 g, 19 mmoles) in dichloromethane (15 ml), kept under nitrogen and cooled to -60° C. Stirring is continued for 15 min. at -60° C. and followed by addition of 2,2-difluoro-1-hydroxy-5-methoxypentane (2.7 g, 17.5 mmoles) in dichloromethane (15 ml). The reaction mixture is stirred for 11/2 hours at -60° C., triethylamine (8.4 ml, 114 mmoles) in dichloromethane (15 ml) is slowly added, and the cooling bath is removed. The reaction mixture is hydrolyzed with brine and diluted with dichloromethane. The organic phase is then washed successively with 2N HCl containing some sodium chloride, and brine. Usual work-up affords the title compound (1.59 g, 53%) which is used for the next step without further purification.

後処理

  1. stirringThe reaction mixture is stirred for 11/2 hours at -60° C.
  2. customthe cooling bath is removed
  3. additiondiluted with dichloromethane
  4. washThe organic phase is then washed successively with 2N HCl containing some sodium chloride, and brine

出典と根拠

ORDレコード
ord-7857d77b235a47458505ec6d65fe4927
出典データセット
uspto-grants-1988_03
特許番号
US04730006

反応ノート

読み込み中…