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

HRID 247526노트

반응식

HRID 247526 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 135481364-(Hydroxymethyl)cyclohexane-1-carbonitrile수율 90%

시약·촉매·용매 1

HCID 14797Potassium Hydroxide용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b7bf4237e1f34981983be5857dbb7323
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04708441

반응 노트

불러오는 중…