Ethyl Thioglycolate → Ethyl 4-[(2-ethoxy-2-oxoethyl)thio]butanoate

HRID 595070

反応式

HRID 595070 の反応式
[Na].[SH:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[CH2:7]([O:6][C:4]([CH2:3][S:2][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:5])[CH3:8]

参加物

5

反応物 3

HCID 12185Ethyl ThioglycolateHCID 18474Ethyl 4-chlorobutyrateHCID 5360545Sodium2 回

生成物 1

HCID 2778847Ethyl 4-[(2-ethoxy-2-oxoethyl)thio]butanoate収率 95.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

Sodium metal (4.3 g, 0.18 mol) was added cautiously in small portions to ethanol (150 mL). After the sodium completely dissolved, the mixture was cooled to 0° C. and ethyl 2-sulfanylacetate (21.9 g, 0.18 mol), was added. Ethyl 4-chlorobutanoate (27.4 g, 0.18 mol) was then added slowly and the resulting mixture stirred overnight at rt. The solid was filtered off, and then the filtrate concentrated under reduced pressure. The oil obtained was partitioned between water and ethyl acetate. The organic layer was collected, dried over anhydrous Na2SO4 and concentrated under vacuum to give the desired ethyl 4-((ethoxycarbonyl)methylthio)butanoate (40.2 g, 95%) as colorless oil. The crude material was used without further purification in the follow step.

後処理

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe oil obtained
  4. customwas partitioned between water and ethyl acetate
  5. customThe organic layer was collected
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-38879612a4614b2f9eb66bbcecbe9b03
出典データセット
uspto-grants-2016_01
特許番号
US09242993B2

関連ノート

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