Trimethylsilyl triflate → HCID 16083429, compound

HRID 1948142Notes

Reaction equation

CO[C:3]1([O:17][CH3:18])[CH2:8][CH2:7][CH:6]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:5][CH2:4]1.C[Si]([C:23]#[N:24])(C)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:10]([O:9][CH:6]1[CH2:5][CH2:4][C:3]([O:17][CH3:18])([C:23]#[N:24])[CH2:8][CH2:7]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1.5 g of (4,4-Dimethoxy-cyclohexyloxymethyl)-benzene (38) were dissolved in 20 mL of dry dichloromethane and cooled to 0° C. 3.05 mL of trimethylsilyl cyanide were added dropwise and after stirring for 2 minutes, 1.31 mL of trimethylsilyl trifluoromethansulfonate were added dropwise. The mixture was stirred at 0° C. for 2 h, then 20 mL of saturated aqueous sodium bicarbonate solution were added dropwise. Phases were separated and the aqueous layer was extracted several times with dichloromethane. The combined organic layer was dried and evaporated to dryness to give 1.5 g of crude product, that was purified by silica gel chromatography to give 1.3 g of the desired compound as a cis-trans-mixture. Rt=4.68 min (Method D). Detected mass: 246.1 (M+H+).

Workup

stirringThe mixture was stirred at 0° C. for 2 h
customPhases were separated
extractionthe aqueous layer was extracted several times with dichloromethane
customThe combined organic layer was dried
customevaporated to dryness
customto give 1.5 g of crude product, that
customwas purified by silica gel chromatography

Sources & evidence

ORD record: ord-8464722f086a46358b9fe746b286937e
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399482B2

Reaction notes

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