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

HRID 660985노트

반응식

HRID 660985 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-aa43d418331a42d69b5c453c0988f090
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084489B2

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