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

HRID 561489노트

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HRID 561489 반응식
[BH4-].[Na+].[Cl: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])=[C:6]([F:17])[CH:5]=1.[Cl-].[NH4+].C(OCC)C>C(O)C.C(OCC)(=O)C>[Cl:3][C:4]1[CH:16]=[CH:15][C:7]([CH:8]([OH:9])[CH:10]2[CH2:12][CH:11]2[C:13]#[N:14])=[C:6]([F:17])[CH:5]=1

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 583924902-(4-Chloro-2-fluorobenzoyl)cyclopropanecarbonitrile

생성물 1

HCID 583922222-[(4-Chloro-2-fluorophenyl)(hydroxy)methyl]cyclopropanecarbonitrile

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

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온도
40 °C

실험 절차

1.01 g (26.6 mmol) of sodium borohydride were added to 5.40 g (24.1 mmol) of the compound from Example 130A in 99 ml of ethanol and 25 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 45 minutes. The reaction mixture was added to saturated aqueous ammonium chloride solution and diethyl ether, the phases were separated, the aqueous phase was extracted twice with diethyl ether, and the combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated. 5.25 g (96% of theory) of a mixture of the diastereomers of the title compound were obtained.

후처리

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted twice with diethyl ether
  3. washthe combined organic phases were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. addition5.25 g (96% of theory) of a mixture of the diastereomers of the title compound
  8. customwere obtained

출처 및 근거

ORD 기록
ord-332b290c8150456fbefdeb171e877268
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063234B2

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