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

HRID 1741955ノート

反応式

HRID 1741955 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-87810d2d7cb04f589f2331b1a888de83
出典データセット
uspto-grants-1994_08
特許番号
US05334740

反応ノート

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