Hydrochloric Acid → HCID 178427752、化合物

HRID 247527ノート

反応式

HRID 247527 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 178427752HCID 178427752、化合物収率 42%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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 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.

後処理

  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

出典と根拠

ORDレコード
ord-eec2a5fc40ee494eb18bff6cf48989ec
出典データセット
uspto-grants-1987_11
特許番号
US04708441

反応ノート

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