Water → 4-Chloro-5-(1-hydroxy-propyl)-thiophene-2-carboxylic acid methyl ester

HRID 660973노트

반응식

HRID 660973 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[S:5][C:6]=1[CH:7]([OH:10])[CH2:8][CH3:9].[C:14]([O-])([O-])=O.[K+].[K+].IC.O>CN(C)C=O>[CH3:14][O:12][C:11]([C:4]1[S:5][C:6]([CH:7]([OH:10])[CH2:8][CH3:9])=[C:2]([Cl:1])[CH:3]=1)=[O:13]

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 674852844-Chloro-5-(1-hydroxy-propyl)-thiophene-2-carboxylic acid

생성물 1

HCID 593559694-Chloro-5-(1-hydroxy-propyl)-thiophene-2-carboxylic acid methyl ester수율 31.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of crude 4-chloro-5-(1-hydroxy-propyl)-thiophene-2-carboxylic acid (0.262 g) in dimethylformamide (6.0 mL) is treated with K2CO3 (0.502 g, 3.63 mmol) and iodomethane (0.17 mL, 2.73 mmol) and stirred overnight. The reaction mixture is then poured into H2O (15 mL) and extracted with EtOAc (3×10 mL). Combined organic extracts are washed with brine (1×), dried over MgSO4, filtered, and concentrated. The residue is loaded onto silica gel and eluted with hexanes using a gradient of 0% to 50% EtOAc to provide 4-chloro-5-(1-hydroxy-propyl)-thiophene-2-carboxylic acid methyl ester (87.6 mg, 15%-2 steps) as a yellow syrup. MS (ES): 216.9 [M+H]+.

후처리

  1. extractionextracted with EtOAc (3×10 mL)
  2. washCombined organic extracts are washed with brine (1×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washeluted with hexanes using a gradient of 0% to 50% EtOAc

출처 및 근거

ORD 기록
ord-1f3c1003aef14d96bcf7be20d1003e50
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084489B2

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