Water → Methyl 5-(1-hydroxy-2-methylpropan-2-yl)thiophene-2-carboxylate

HRID 660985ノート

反応式

HRID 660985 の反応式
[OH:1][CH2:2][C:3]([C:6]1[S:10][C:9]([C:11]([OH:13])=[O:12])=[CH:8][CH:7]=1)([CH3:5])[CH3:4].[C:14]([O-])([O-])=O.[K+].[K+].IC.O>CN(C=O)C>[CH3:14][O:12][C:11]([C:9]1[S:10][C:6]([C:3]([CH3:4])([CH3:5])[CH2:2][OH:1])=[CH:7][CH:8]=1)=[O:13]

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 674845155-(2-Hydroxy-1,1-dimethyl-ethyl)-thiophene-2-carboxylic acid

生成物 1

HCID 67484466Methyl 5-(1-hydroxy-2-methylpropan-2-yl)thiophene-2-carboxylate収率 83%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 5-(2-hydroxy-1,1-dimethyl-ethyl)-thiophene-2-carboxylic acid (0.495 g, 2.47 mmol) in DMF (12.0 mL) is treated with K2CO3 (0.515 g, 3.73 mmol), iodomethane (0.23 mL, 3.69 mmol), and stirred at rt overnight. The mixture is poured into H2O (25 mL) and extracted with EtOAc (3×25 mL). The combined extracts are washed with H2O, brine, dried over MgSO4, filtered, and concentrated. The residue is loaded onto silica gel and eluted with hexanes using a gradient of 0% to 75% EtOAc to give 5-(2-hydroxy-1,1-dimethyl-ethyl)-thiophene-2-carboxylic acid methyl ester (0.439 g, 83%). MS (ES): 215.1 [M+H]+.

後処理

  1. extractionextracted with EtOAc (3×25 mL)
  2. washThe combined extracts are washed with H2O, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washeluted with hexanes using a gradient of 0% to 75% EtOAc

出典と根拠

ORDレコード
ord-aa43d418331a42d69b5c453c0988f090
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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