Sodium hydride → Ethyl 2-(Cyclopropylthio)-2,2-Difluoroacetate

HRID 1976923ノート

反応式

HRID 1976923 の反応式
[CH:1]1([SH:4])[CH2:3][CH2:2]1.C1(Br)CC1.[H-].[Na+].Br[C:12]([F:19])([F:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14]>CS(C)=O.CCOCC>[CH:1]1([S:4][C:12]([F:19])([F:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:3][CH2:2]1

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 69585Ethyl bromodifluoroacetateHCID 78037BromocyclopropaneHCID 4713099Cyclopropanethiol

生成物 1

HCID 21999458Ethyl 2-(Cyclopropylthio)-2,2-Difluoroacetate収率 46%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 3283Diethyl Ether溶媒

実験手順

An ether solution of cyclopropyl mercaptan synthesized from cyclopropyl bromide (50.0 g, 413 mmol) in accordance with the process described in literature (J. Am. Chem. Soc., 114, 3492 (1992)) was added dropwise to a solution of 60% sodium hydride (5.4 g, 135 mmol) in dimethyl sulfoxide (100 ml) under cooling with ice, and the mixture was stirred at room temperature for 10 minutes. A solution of ethyl bromodifluoroacetate (27.4 g, 135 mmol) in dimethyl sulfoxide (200 ml) was added dropwise to this solution under cooling with ice, and the resultant mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was poured into ice water to conduct extraction with ether. The solvent was distilled out of the resultant extract under reduced pressure. The resultant residue was distilled under reduced pressure to obtain the intended product (12.3 g; yield: 46.0%) as a colorless oil.

後処理

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. customAfter completion of the reaction
  4. extractionextraction with ether
  5. distillationThe solvent was distilled out of the resultant
  6. extractionextract under reduced pressure
  7. distillationThe resultant residue was distilled under reduced pressure
  8. customto obtain the intended product (12.3 g; yield: 46.0%) as a colorless oil

出典と根拠

ORDレコード
ord-668bcdfe8bd94f47a31974dc629ff4d3
出典データセット
uspto-grants-2001_05
特許番号
US06229049B1

反応ノート

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