Hydrochloric Acid → HCID 178427752, 화합물

HRID 1583226노트

반응식

HRID 1583226 반응식
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([C:9]#[N:10])[CH2:5][CH2:4]1.[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.O.Cl>N1C=CC=CC=1>[S:18]([O:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]#[N:10])[CH2:5][CH2:4]1)([C:15]1[CH:16]=[CH:17][C:12]([CH3:11])=[CH:13][CH:14]=1)(=[O:20])=[O:19].[S:18]([O:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]#[N:10])[CH2:5][CH2:4]1)([C:15]1[CH:16]=[CH:17][C:12]([CH3:11])=[CH:13][CH:14]=1)(=[O:20])=[O:19]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 135481364-(Hydroxymethyl)cyclohexane-1-carbonitrile

생성물 2

HCID 178427751HCID 178427751, 화합물수율 41%HCID 178427752HCID 178427752, 화합물수율 42%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A solution of 1.20 g of the 4-(hydroxymethyl)cyclohexanecarbonitrile obtained in 5 ml of pyridine was treated portionwise at room temperature and under argon gasification with 2.46 g of p-tosyl chloride. After stirring at room temperature for 3.5 hours (formation of a white precipitate), the mixture, cooled to 0° C., was treated with about 2 ml of water, cautiously made acid with about 7 ml of concentrated hydrochloric acid and extracted three times with 30 ml of diethyl ether each time. The organic phases were washed with 50 ml of water and 50 ml of saturated sodium chloride solution, dried over magnesium sulphate and concentrated, 2.31 g of semi-crystalline oil remaining behind. Low-pressure chromatography (0.5 bar) on 480 g of silica gel using 30% ethyl acetate/petroleum ether as the eluant gave 1.06 g (42%) of trans-4-(tosyloxymethyl)cyclohexanecarbonitrile as a colourless cyrstallizing oil (m.p. 84°-85° C.) and 1.03 g (41%) of cis-4-(tosyloxymethyl)cyclohexanecarbonitrile as a colourless viscous oil. Rf-values (30% ethyl acetate/petroleum ether): trans product 0.25, cis product 0.20.

후처리

  1. temperaturecooled to 0° C.
  2. extractionextracted three times with 30 ml of diethyl ether each time
  3. washThe organic phases were washed with 50 ml of water and 50 ml of saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e99b5d7167e64a63b1317503dff5b818
출처 데이터셋
uspto-grants-1985_11
특허 번호
US04550981

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