Hydrochloric Acid → HCID 178427752, 화합물

HRID 1462616노트

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HRID 1462616 반응식
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([C:9]#[N:10])[CH2:5][CH2:4]1.[S:11](Cl)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12].O.Cl>N1C=CC=CC=1>[S:11]([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:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12]

참가 물질

6

반응물 4

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

생성물 1

HCID 178427752HCID 178427752, 화합물

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 with 2.46 g of tosyl chloride at room temperature and while gassing with argon. 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, there remaining behind 2.31 g of a semi-crystalline oil. Low-pressure chromatography (0.5 bar) on 480 g of silica gel using 30% ethyl acetate/petroleum ether as the eluant gave 1.06 (42%) of trans-4-(tosyloxymethyl)cyclohexanecarbonitrile as a colourless, crystallizing 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-e09eca4939fa45759084dc3b8a0e98ef
출처 데이터셋
uspto-grants-1984_07
특허 번호
US04460770

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