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

HRID 561489ノート

反応式

HRID 561489 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-332b290c8150456fbefdeb171e877268
出典データセット
uspto-grants-2011_11
特許番号
US08063234B2

反応ノート

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