Water → 4-(Hydroxymethyl)cyclohexane-1-carbonitrile

HRID 1583225ノート

反応式

HRID 1583225 の反応式
[C:1]([CH:3]1[CH2:8][CH2:7][CH:6]([CH:9]=[O:10])[CH2:5][CH2:4]1)#[N:2].[BH4-].[Na+].O>[OH-].[K+]>[OH:10][CH2:9][CH:6]1[CH2:7][CH2:8][CH:3]([C:1]#[N:2])[CH2:4][CH2:5]1

参加物

5

反応物 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 13548132trans-4-Formylcyclohexanecarbonitrile

生成物 1

HCID 135481364-(Hydroxymethyl)cyclohexane-1-carbonitrile収率 90%

試薬・触媒・溶媒 1

HCID 14797Potassium Hydroxide溶媒

反応条件

温度
0 °C

実験手順

A solution of 1.34 g of 4-cyanocyclohexanecarboxaldehyde (cis/trans mixture) in 40 ml of 0.1N methanolic potassium hydroxide solution was treated portionwise at 0° C. under argon gasification with 378 mg of solid sodium borohydride. After completion of the addition, the mixture was stirred at 0° C. for a further 20 minutes, then 50 ml of water were added and the mixture was extracted three times with 50 ml of methylene chloride each time. The organic phases were washed twice with 50 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.4 bar) of the residual oil on silica gel with chloroform/ethyl acetate (1:1) gave 1.22 g (90%) of 4-(hydroxymethyl)cyclohexanecarbonitrile (likewise as an about 1:1 mixture of the two epimers) as a colourless viscous oil. This material was used in the following tosylation without further purification. Rf-value of 4-(hydroxymethyl)cyclohexanecarbonitrile [chloroform/ethyl acetate (1:1)]: 0.29 (longish spot).

後処理

  1. additionAfter completion of the addition
  2. extractionthe mixture was extracted three times with 50 ml of methylene chloride each time
  3. washThe organic phases were washed twice with 50 ml of water each time
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-a6c59b038e204fb5b7de5c2adc5e3625
出典データセット
uspto-grants-1985_11
特許番号
US04550981

反応ノート

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