Sodium Chloride → HCID 178489252, compound

Participants

Reaction Conditions

Reaction Steps

Thioacetal 5 (227 mg, 0.7 mmol, 1 eq.) and 1 mL of benzyl chloromethyl ether (546 mg, 3.5 mmol, 5 eq., 60% of reagent in the commercial source) was dissolved in anhydrous THF (35 mL) and the solution was cooled to −78° C. To the stirred solution 1.54 M n-butyllithium in hexane (1 mL, 1.54 mmol, 2.2 eq.) was added dropwise over a period of 10 min. After the mixture was stirred for 10 min at −78° C. the reaction was allowed to warm up to room temperature. It took about 30 min. The TLC shows one major product and no starting material. Saturated NaCl solution was added into the reaction mixture and the red solution was extracted with dichloromethane. The dichloromethane solution was washed with water twice, dried under MgSO4 and concentrated under reduced pressure. The oily residue was separated via column chromatography on silica gel to give 185 mg of disubstituted product 9 (47%). 1H NMR (CDCl3, TMS, ppm) δ: 7.38 (m, 10H), 7.31 (d, J=8.7 Hz, 2H), 6.86 (d, J=8.5 Hz, 2H), 5.00 (s, 4.76 (d, J=12.3 Hz, 1H), 4.74 (d, J=12.0 Hz, 1H), 4.71 (d, J=11.0 Hz, 1H), 4.61 (d, J=12.0 Hz, 1H), 4.57 (d, J=12.3 Hz, 1H), 4.49 (d, J=10.6 Hz, 1H), 4.30 (d, J=10.7 Hz, 1H), 3.83 (d, J=11.1 Hz, 1H), 3.80 (s, 3H), 3.29 (s, 3H), 3.20 (s, 3H). FAB-MS: Calcd for C30H32N2O5S2: 564.1. Found [M+H]+: 565.1.

Provenance & Evidence