Water → 2-[Hydroxy(4-methylphenyl)methyl]cyclopropanecarbonitrile

HRID 561482노트

반응식

HRID 561482 반응식
[BH4-].[Na+].[CH3:3][C:4]1[CH:16]=[CH:15][C:7]([C:8]([CH:10]2[CH2:12][CH:11]2[C:13]#[N:14])=[O:9])=[CH:6][CH:5]=1.O>C(O)C.C(OCC)(=O)C>[OH:9][CH:8]([C:7]1[CH:6]=[CH:5][C:4]([CH3:3])=[CH:16][CH:15]=1)[CH:10]1[CH2:12][CH:11]1[C:13]#[N:14]

참가 물질

6

반응물 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 583924152-(4-Methylbenzoyl)cyclopropanecarbonitrile

생성물 1

HCID 583923442-[Hydroxy(4-methylphenyl)methyl]cyclopropanecarbonitrile

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

반응 조건

온도
40 °C

실험 절차

607 mg (16.0 mmol) of sodium borohydride were added to 2.70 g (14.6 mmol) of the compound from Example 126A in 60 ml of ethanol and 16 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 2 h. The reaction mixture was added to water and extracted with dichloromethane, and the organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) to result in 2.56 g (94% of theory) of a mixture of the diastereomers of the title compound.

후처리

  1. extractionextracted with dichloromethane
  2. washthe organic phase was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient)

출처 및 근거

ORD 기록
ord-813536802ef449fca12bbcf7d7b84346
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063234B2

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