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Dichloromethane → 2-[(2-Chloro-4-fluorophenyl)(hydroxy)methyl]cyclopropanecarbonitrile

HRID 561485
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HRID 561485 반응식
[BH4-].[Na+].[Cl:3][C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[C:6]([CH:8]1[CH2:10][CH:9]1[C:11]#[N:12])=[O:7].ClCCl>C(O)C.C(OCC)(=O)C>[Cl:3][C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[CH:6]([OH:7])[CH:8]1[CH2:10][CH:9]1[C:11]#[N:12]
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참가 물질

6

반응물 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 583925012-(2-Chloro-4-fluorobenzoyl)cyclopropanecarbonitrile

생성물 1

HCID 583924412-[(2-Chloro-4-fluorophenyl)(hydroxy)methyl]cyclopropanecarbonitrile

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate
용매

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온도
40 °C

실험 절차

409 mg (10.8 mmol) of sodium borohydride were added to 2.20 g (9.84 mmol) of the compound from Example 127A in 180 ml of ethanol and 60 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 2 h. The reaction mixture was added to dichloromethane, the phases were separated, 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 1.52 g (69% of theory) of a mixture of the diastereomers of the title compound.

후처리

  1. customthe phases were separated
  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-3f7694c970b54369b45e3665c2a5eb88
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08063234B2

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