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

HRID 561483
ノート
印刷プレビュー

反応式

HRID 561483 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒
HCID 8857
Ethyl Acetate
溶媒

反応条件

温度
40 °C

実験手順

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.

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 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

出典と根拠

ORDレコード
ord-fc5f375805a94fe8af6a928964fd7edd
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08063234B2

反応ノート

読み込み中…

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