Potassium Cyanide → Chroman-3-yl-acetonitrile

HRID 1032386노트

반응식

HRID 1032386 반응식
[C-:1]#[N:2].[K+].C1(C)C=CC(S(O[CH2:14][CH:15]2[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[O:17][CH2:16]2)(=O)=O)=CC=1>CS(C)=O>[C:1]([CH2:14][CH:15]1[CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[O:17][CH2:16]1)#[N:2]

참가 물질

4

반응물 2

HCID 9032Potassium CyanideHCID 11267124Toluene-4-sulfonic acid Chroman-3-ylmethyl ester

생성물 1

HCID 14838407Chroman-3-yl-acetonitrile수율 88.3%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

12.53 g (192.5 mmol) of potassium cyanide are added at room temperature to a solution of 55.72 g (175 mmol) of 3-(p-toluenesulphonyloxymethyl)chroman (for manufacture see Example 1) in 300 ml of dimethyl sulphoxide and the whole is heated to 60° while stirring. After 3 hours, ice-water is added to the reaction mixture, the whole is extracted with diethyl ether and washed thoroughly with water. The combined organic phases are dried over sodium sulphate and concentrated by evaporation in vacuo. 26.75 g (88.3%) of 3-cyanomethylchroman are obtained in the form of a pale yellow oil which crystallises from diethyl ether/pentane. The crystals melt at 63°.

후처리

  1. temperaturethe whole is heated to 60°
  2. extractionthe whole is extracted with diethyl ether
  3. washwashed thoroughly with water
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. concentrationconcentrated by evaporation in vacuo

출처 및 근거

ORD 기록
ord-51c7fa19d775459d83b9a767443e0f77
출처 데이터셋
uspto-grants-1990_09
특허 번호
US04957928

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