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

HRID 1741955Notes

Reaction equation

HRID 1741955 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-87810d2d7cb04f589f2331b1a888de83
Source dataset
uspto-grants-1994_08
Patent number
US05334740

Reaction notes

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