(Diethylamino)sulfur trifluoride → 4-Fluoro-4-methyl-pent-2-ynoic acid ethyl ester

HRID 734366ノート

反応式

HRID 734366 の反応式
[CH2:1]([O:3][C:4](=[O:11])[C:5]#[C:6][C:7](O)([CH3:9])[CH3:8])[CH3:2].CCN(S(F)(F)[F:18])CC>ClCCl>[CH2:1]([O:3][C:4](=[O:11])[C:5]#[C:6][C:7]([F:18])([CH3:9])[CH3:8])[CH3:2]

参加物

4

反応物 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 112289264-Hydroxy-4-methyl-pent-2-ynoic acid ethyl ester

生成物 1

HCID 866170244-Fluoro-4-methyl-pent-2-ynoic acid ethyl ester収率 100%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

A solution of 4-hydroxy-4-methyl-pent-2-ynoic acid ethyl ester (4.9 g, 155 mmol) in dichloromethane (30 mL) was cooled to −78° C. and treated with DAST (5.3 g, 161.2 mmol) the reaction mixture was stirred for 2 h at −78° C. then warmed to room temperature and poured over ice. After the ice had melted, the phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried (sodium sulfate) and concentrated on a rotary evaporator to provide 5.0 g (100%) of 4-fluoro-4-methyl-pent-2-ynoic acid ethyl ester as a brown oil.

後処理

  1. temperaturethen warmed to room temperature
  2. additionpoured over ice
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted with dichloromethane
  5. dry with materialThe combined organic phases were dried (sodium sulfate)
  6. concentrationconcentrated on a rotary evaporator

出典と根拠

ORDレコード
ord-6077568ff76a4ae0abc333116b07213c
出典データセット
uspto-grants-2009_09
特許番号
US07592353B2

反応ノート

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