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

HRID 30493

반응식

HRID 30493 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 241Benzene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e0866e356d694e0da29bc5cae5ef3ed2
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423152B2

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