Chlorotrimethylsilane → HCID 22357954, compound

HRID 1484481Notes

Reaction equation

Cl[Si:2]([CH3:5])([CH3:4])[CH3:3].[OH:6][CH2:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1.C(N(CC)CC)C>C1COCC1>[CH3:3][Si:2]([CH3:5])([CH3:4])[O:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Chlorotrimethylsilane (2.3 mL, 18.4 mmol) was added dropwise to a solution of methyl 4-(hydroxymethyl)benzoate (2.0 g, 12.0 mmol) and triethylamine (3.3 mL, 23.7 mmol) in anhydrous THF (80 ml) cooled to 0° C. A precipitate formed and the stirring was continued at 0° C. for 1 h. The mixture was diluted with hexanes (50 mL) and precipitates eliminated by vacuum filtration through a sintered funnel. Volatiles were removed by rotary evaporation. The residue was purified by flash chromatography (DCM:Hex 1:1+1% TEA) through a short silica column providing methyl 4-[(trimethylsiloxy)methyl]benzoate as a clear liquid in a yield of 2.5 g (87%). 1H-NMR (500 MHz, CDCl3): δ=0.16 ppm (s, 9H), 3.90 ppm (s, 3H), 4.74 ppm (s, 2H), 7.38 ppm (d, J=8.0 Hz, 2H), 8.00 ppm (d, J=8.0 Hz, 2H); 13C-NMR (500 MHz, CDCl3): δ=−0.41, 52.09, 64.12, 126.08, 128.90, 129.68, 146.39, 167.10 ppm. HRMS [+Scan]; calculated m/z for C12H19O3Si 239.1098; observed mass: 239.1095.

Workup

customA precipitate formed
customprecipitates
filtrationeliminated by vacuum filtration through a sintered funnel
customVolatiles were removed by rotary evaporation
customThe residue was purified by flash chromatography (DCM:Hex 1:1+1% TEA) through a short silica column

Sources & evidence

ORD record: ord-6ab37e2bf2c6468588760d909b210b8f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422232B2

Reaction notes

Loading…