Ammonium Chloride → 2-Cyclohexyl-2-hydroxy-2-thien-2-ylacetic Acid Methyl Ester

HRID 1366723ノート

反応式

HRID 1366723 の反応式
[CH:1]1([Mg]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:9][O:10][C:11](=[O:19])[C:12](=[O:18])[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1.[Cl-].[NH4+]>C(OCC)C.C1COCC1>[CH3:9][O:10][C:11](=[O:19])[C:12]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([OH:18])[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 11217486Methyl alpha-oxo-2-thiopheneacetateHCID 178478990HCID 178478990、化合物

生成物 1

HCID 669594652-Cyclohexyl-2-hydroxy-2-thien-2-ylacetic Acid Methyl Ester

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

98.6 ml (0.197 mol) of a 2M solution of Cyclohexylmagnesium chloride in diethyl ether, were added to a solution of 27.97 g (0.164 mol) of 2-oxo-2-thien-2-ylacetic acid methyl ester dissolved in 370 ml of THF, at −78° C. under a N2atmosphere. The mixture was stirred at this temperature for 10 minutes, and then warmed to room temperature. After 1 h, the reaction mixture was treated with a saturated solution of ammonium chloride and extracted three times with ethyl acetate. The organic phases were combined, washed with water, and dried over MgSO4. After removal of the solvent, the oil obtained was purified by column chromatography (silica gel) using hexane/AcOEt 90:10 as eluent. The yield was 16.2 g (39.5%) of a pure product, whose structure was confirmed by 1H-NMR.

後処理

  1. waitAfter 1 h
  2. extractionextracted three times with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customAfter removal of the solvent
  6. customthe oil obtained
  7. customwas purified by column chromatography (silica gel)

出典と根拠

ORDレコード
ord-bab23b4e690b487b86fc0805fabb21c1
出典データセット
uspto-grants-2011_02
特許番号
US07893087B2

反応ノート

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