Methanol → HCID 178490207, compound

Participants

Reaction Steps

To a cooled solution of 3-[(tert-Butyldimethylsilyl)oxy]-4-methoxybenzylthio acetic acid 16 (8.75 g, 25.5 mmol) in tetrahydrofuran (40 mL) was added 1.0 M solution of tetra-n-butyl ammonium fluoride in tetrahydrofuran (6.68 g or 25.54 mL, 25.5 mmol) slowly and stirred under nitrogen for 2 h at room temperature. The progress of the reaction was monitored by TLC (9:1—chloroform:methanol on silica gel plate). Water was added to the reaction mixture and extracted with ethyl acetate. The organic layer was washed with water and dried. Removal of the solvent in vacuo yielded a semi solid that was subjected to column chromatography (initial with chloroform and finally with ethyl acetate) afforded the pure product 17. Yield: 50%; white solid mp 128-130° C. 1H NMR: δ 3.34 (s, 2H, CH2), 3.84 (s, 3H, OCH3), 4.04 (s, 2H, CH2), 6.80-7.01 (m, 3H, Ar—H). Anal. Calcd for C10H12O4S: C, 52.62, H, 5.30. Found: C, 52.58, H, 5.35.

Provenance & Evidence