Imidazole → 4,5-(Dimethylmethylenedioxy)-3-(tert-butyldimethylsilyloxy)6-heptenenitrile

HRID 1741955노트

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HRID 1741955 반응식
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:9][C:10]1([CH3:22])[O:21][CH:18]([CH:19]=[CH2:20])[CH:12]([CH:13]([OH:17])[CH2:14][C:15]#[N:16])[O:11]1.N1C=CN=C1.C(Cl)Cl>C(OCC)C>[CH3:9][C:10]1([CH3:22])[O:21][CH:18]([CH:19]=[CH2:20])[CH:12]([CH:13]([O:17][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:14][C:15]#[N:16])[O:11]1

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 190109954,5-(Dimethylmethylenedioxy)-3-hydroxy-6-heptenenitrile

생성물 1

HCID 190109964,5-(Dimethylmethylenedioxy)-3-(tert-butyldimethylsilyloxy)6-heptenenitrile수율 79%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

Two grams of tert-butyldimethylsilyl chloride were gradually added at 0° C. to a solution comprising 2.11 g of 4,5-(dimethylmethylenedioxy)-3-hydroxy-6-heptenenitrile, 2.0 g of imidazole and 50 ml of methylene chloride. After stirring was conducted at room temperature for 16 hours, the reaction mixture was diluted with 300 ml of diethyl ether, and washed with 1N hydrochloric acid, a saturated sodium hydrogen carbonate aqueous solution and a sodium chloride aqueous solution in sequence. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to afford 2.63 g of 4,5-(dimethylmethylenedioxy)-3-(tert-butyldimethylsilyloxy)6-heptenenitrile having the following properties (yield 79%).

후처리

  1. washwashed with 1N hydrochloric acid
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-87810d2d7cb04f589f2331b1a888de83
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05334740

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