Chloroform → 3-[(tert-Butyldimethylsilyl)oxy]-4-methoxybenzyl Chloride

HRID 1028924Notes

Reaction equation

[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH2:12]O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].S(Cl)([Cl:21])=O.C(Cl)(Cl)Cl>C1C=CC=CC=1>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH2:12][Cl:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled solution of 3-[(tert-Butyldimethylsilyl)oxy]-4-methoxybenzyl alcohol 14 (9.5 g, 35.4 mmol) in benzene (50 mL) under nitrogen, thionyl chloride (6.32 g or 3.87 mL, 53.1 mmol) dissolved in benzene (5 mL) was added over 10 min and maintained the temperature at 0° C. for 2 h. The completion of reaction was checked by TLC (chloroform on silica gel plate). Ice was added to the reaction mixture and the solution was extracted with ethylacetate. The organic layer was washed with saturated bicarbonate solution and water and dried over anhydrous sodium sulfate. Removal of the solvent in vacuo afforded 15. Yield: 98.5%; yellow oil. 1H NMR: δ 0.16 (s, 6H, 2×CH3), 1.00 (s, 9H, 3×CH3), 3.80 (s, 3H, OCH3), 4.44 (s, 2H, CH2), 6.70-7.01 (m, 3H, Ar—H). Anal. Calcd for C14H23ClO2Si: C, 58.62, H, 8.08. Found: C, 58.69, H, 8.03.

Workup

additionwas added over 10 min
customThe completion of reaction
additionIce was added to the reaction mixture
extractionthe solution was extracted with ethylacetate
washThe organic layer was washed with saturated bicarbonate solution and water
dry with materialdried over anhydrous sodium sulfate
customRemoval of the solvent in vacuo

Sources & evidence

ORD record: ord-3e09aaf98e064a839ddb1d40729ab401
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735620B2

Reaction notes

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