Pyridine → HCID 14805748, 화합물

HRID 1659820노트

반응식

HRID 1659820 반응식
[CH3:1][C@H:2]([CH2:6][CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH2:3][CH2:4][OH:5].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.N1C=CC=CC=1>C(Cl)(Cl)Cl>[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([O:5][CH2:4][CH2:3][C@H:2]([CH3:1])[CH2:6][CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])(=[O:20])=[O:19])=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 6999991(3R)-3,7-Dimethyl-1-octanol

생성물 1

HCID 14805748HCID 14805748, 화합물수율 89%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A solution of 6.5 g (41 mmol) of (R)-3,7-dimethyl-1-octanol and 7.8 g (41 mmol) of p-toluenesulphonyl chloride in 50 ml of absolute chloroform is treated at 0° with 7.9 g (0.1 mol) of absolute pyridine. The mixture is subsequently stirred at 4° for 20 hours. For the working-up the mixture is poured on to 500 g of ice and extracted three times with chloroform. The combined organic phases are washed first with cold 1-N hydrochloric acid, then with saturated aqueous sodium bicarbonate solution and subsequently with saturated aqueous common salt solution. After drying over potassium carbonate and removal of the solvent under reduced pressure, the crude product is chromatographed on 300 g of silicagel with benzene. There are obtained 11.4 g (89%) of (R)-3,7-dimethyl-1-octanol p-toluenesulphonate; [α]D20 =+2.0 (c=4.0, benzene).

후처리

  1. extractionextracted three times with chloroform
  2. washThe combined organic phases are washed first with cold 1-N hydrochloric acid
  3. dry with materialAfter drying over potassium carbonate and removal of the solvent under reduced pressure
  4. customthe crude product is chromatographed on 300 g of silicagel with benzene

출처 및 근거

ORD 기록
ord-33cbb262cef4425d8d9d2abfeed3311a
출처 데이터셋
uspto-grants-1981_12
특허 번호
US04305876

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