Water → methyl 2-(2-thienylthio)acetate

HRID 1597421ノート

反応式

HRID 1597421 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[SH:6].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:14][C:15]([O:17][CH3:18])=[O:16].O>CN(C=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6][CH2:14][C:15]([O:17][CH3:18])=[O:16]

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 5226742-Thiophenethiol

生成物 1

HCID 12201118methyl 2-(2-thienylthio)acetate収率 79%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of thiophene-2-thiol (1.2 g, 10.3 mmol) in anhydrous DMF (30 mL) was added cesium carbonate (3.9 g, 12 mmol) and the resulting suspension was stirred for 15 min at ambient temperature, then treated with methyl bromoacetate (1.53 g, 10 mmol). The purple suspension was stirred for 1 h, then poured into water (30 mL) and extracted twice with 300 mL EtOAc. The combined organic extracts were washed with brine, dried, filtered, concentrated and the residue was purified via column chromatography eluting with 10% EtOAc/Hexanes to give 1.48 g (79%) of the title compound.

後処理

  1. stirringThe purple suspension was stirred for 1 h
  2. extractionextracted twice with 300 mL EtOAc
  3. washThe combined organic extracts were washed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified via column chromatography
  8. washeluting with 10% EtOAc/Hexanes

出典と根拠

ORDレコード
ord-1263f8e6962745d6ac0cb9b0e2d826d8
出典データセット
uspto-grants-2001_09
特許番号
US06294573B1

反応ノート

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