Water → 2-[Hydroxy(4-methylphenyl)methyl]cyclopropanecarbonitrile

HRID 561482ノート

反応式

HRID 561482 の反応式
[BH4-].[Na+].[CH3:3][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])=[CH:6][CH:5]=1.O>C(O)C.C(OCC)(=O)C>[OH:9][CH:8]([C:7]1[CH:6]=[CH:5][C:4]([CH3:3])=[CH:16][CH:15]=1)[CH:10]1[CH2:12][CH:11]1[C:13]#[N:14]

参加物

6

反応物 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 583924152-(4-Methylbenzoyl)cyclopropanecarbonitrile

生成物 1

HCID 583923442-[Hydroxy(4-methylphenyl)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

607 mg (16.0 mmol) of sodium borohydride were added to 2.70 g (14.6 mmol) of the compound from Example 126A in 60 ml of ethanol and 16 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 2 h. The reaction mixture was added to water and extracted with dichloromethane, 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 2.56 g (94% of theory) of a mixture of the diastereomers of the title compound.

後処理

  1. extractionextracted with dichloromethane
  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)

出典と根拠

ORDレコード
ord-813536802ef449fca12bbcf7d7b84346
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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