2-Oxobutanoic Acid → 2-oxo-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

HRID 30493

反応式

HRID 30493 の反応式
[O:1]=[C:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4].[C:8]1([C:14]([CH3:24])([CH3:23])[CH:15]2[CH2:20][CH2:19][CH:18]([CH3:21])[CH2:17][CH:16]2O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:21][C@H:18]1[CH2:17][C@@H:16]([O:4][C:3](=[O:5])[C:2](=[O:1])[CH2:6][CH3:7])[C@H:15]([C:14]([CH3:24])([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH3:23])[CH2:20][CH2:19]1

参加物

5

反応物 2

HCID 582-Oxobutanoic AcidHCID 577105(+)-8-Phenylmenthol

生成物 1

HCID 110883962-oxo-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester収率 92.5%

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 241Benzene溶媒

実験手順

A solution of 2.28 g 2-oxobutyric acid (2, 22.11 mmol, 1.3 eq), 4.04 g (−)-8-phenylmenthol (18, 17.02 mmol, 1.0 eq) and 169.9 mg para-toluenesulfonic acid monohydrate (0.884 mmol, 0.52 eq) in 48 mL benzene was heated to reflux for 20 h 35 min. After cooling down to room temperature, the solution was washed twice with 50 mL saturated aqueous sodium hydrogencarbonate solution, and subsequently with 50 mL water and 50 mL brine. The organic phase was dried over 5 g sodium sulfate and was filtered. The filter cake was washed with 10 mL benzene. The organic phase was evaporated to dryness in a rotary evaporator (40° C., 20 mbar) yielding the title compound (4.98 g, 92% by weight) as colorless solid.

後処理

  1. temperatureto reflux for 20 h 35 min
  2. washthe solution was washed twice with 50 mL saturated aqueous sodium hydrogencarbonate solution
  3. dry with materialThe organic phase was dried over 5 g sodium sulfate
  4. filtrationwas filtered
  5. washThe filter cake was washed with 10 mL benzene
  6. customThe organic phase was evaporated to dryness in a rotary evaporator (40° C., 20 mbar)

出典と根拠

ORDレコード
ord-e0866e356d694e0da29bc5cae5ef3ed2
出典データセット
uspto-grants-2008_09
特許番号
US07423152B2

関連ノート

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