Water → methyl 2-(2-thienylthio)acetate

HRID 1597421노트

반응식

HRID 1597421 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 12201118methyl 2-(2-thienylthio)acetate수율 79%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1263f8e6962745d6ac0cb9b0e2d826d8
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06294573B1

반응 노트

불러오는 중…