Chlorotrimethylsilane → Methyl 6-phenyl-4-[(trimethylsilyl)-oxy]-hexa-3,5-dienoate

HRID 37608Notes

Reaction equation

[O:1]=[C:2](/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[CH3:17][Si:18]([CH3:21])([CH3:20])Cl.N12CCCCC1C=NCCC2>C(OCC)C>[C:11]1([CH:10]=[CH:9][C:2]([O:1][Si:18]([CH3:21])([CH3:20])[CH3:17])=[CH:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3 g of the product of Step B, 45 ml of diethyl ether and 2.2 ml of trimethylchlorosilane were mixed together and after the mixture was cooled to 0° C., then 2.5 ml of 1,5-diaza-5-bicyclo-[5,4,0]-undecene (DBU) and 20 ml of diethyl ether were added. The mixture was stirred while allowing the temperature to rise to 20° to 21° C. for one hour. After filtration, the ether was evaporated off to obtain 4.2 g of the desired product which was used as is in the following step.

Workup

filtrationAfter filtration
customthe ether was evaporated off

Sources & evidence

ORD record: ord-b44b95a23abd47a49ef15184cef75a81
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420340

Reaction notes

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