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

HRID 660973ノート

反応式

HRID 660973 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-1f3c1003aef14d96bcf7be20d1003e50
出典データセット
uspto-grants-2011_12
特許番号
US08084489B2

反応ノート

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