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Diethyl Ether → (4-Chlorophenyl)(2,2-difluorocyclopropyl)methanol

HRID 561483
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HRID 561483 반응식
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH:12]2[CH2:14][C:13]2([F:16])[F:15])=[O:11])=[CH:6][CH:5]=1.[Cl-].[NH4+].C(OCC)C>C(O)C.C(OCC)(=O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH:12]2[CH2:14][C:13]2([F:15])[F:16])[OH:11])=[CH:8][CH:9]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 248658712,2-Difluorocyclopropyl(4-chlorophenyl) ketone

생성물 1

HCID 58392413(4-Chlorophenyl)(2,2-difluorocyclopropyl)methanol

시약·촉매·용매 2

HCID 702Ethanol용매
HCID 8857
Ethyl Acetate
용매

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온도
40 °C

실험 절차

336 mg (8.89 mmol) of sodium borohydride were added to 1.75 g (8.08 mmol) of the compound from Example 124A in 33 ml of ethanol and 9 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 1 h. 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 magnesium sulfate, filtered and concentrated. 1.44 g (82% 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 magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. addition1.44 g (82% of theory) of a mixture of the diastereomers of the title compound
  8. customwere obtained

출처 및 근거

ORD 기록
ord-fc5f375805a94fe8af6a928964fd7edd
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08063234B2

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