Imidazole → 4-(Tert-butyldimethylsiloxy)-1,6-heptadiene

HRID 549510

Reaction equation

N1C=CN=C1.[CH2:6]=[CH:7][CH2:8][CH:9]([OH:13])[CH2:10][CH:11]=[CH2:12].[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>O>[O:13]([CH:9]([CH2:10][CH:11]=[CH2:12])[CH2:8][CH:7]=[CH2:6])[Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

There were supplied 6.5 g of imidazole manufactured by Wako Pure Chemical Industries, Ltd. to a 100 mL-two neck flask, and thereto, 50 mL of anhydrous N,N-dimethylformaide manufactured by Wako Pure Chemical Industries, Ltd., and 5.78 mL of 1,6-heptadien-4-ol manufactured by Aldrich Chemical Company were added. The obtained mixture was cooled down to 0° C. To the mixture, 6.5 g of tert-butyldimethylsilyl chloride manufactured by Tokyo Chemical Industry Co., Ltd. were added, and the resultant mixture was stirred for 12 hours at a room temperature. Then, an excess amount of water was added thereto, thereby terminating the reaction. A product contained in the reaction mixture was extracted with hexane, and the obtained organic extract was dried over anhydrous sodium sulfate manufactured by Nacalai Tesque, Inc. The dried hexane solution was distilled in vacuo, thereby obtaining 2.88 g (yield: 30%) of 4-(tert-butyldimethylsiloxy)-1,6-heptadiene as clear colorless oil.

Workup

additionwere added
additionwere added
customterminating
customthe reaction
extractionwas extracted with hexane
extractionthe obtained organic extract
dry with materialwas dried over anhydrous sodium sulfate
distillationThe dried hexane solution was distilled in vacuo

Sources & evidence

ORD record: ord-99c9cfe783294f808c34d76816e5b6dd
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943715B2

Linked notes

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