Tetrabutylammonium Fluoride → HCID 70131253, compound

Participants

Reaction Steps

A solution of 150 mg (0.33 mmol) of 1-[10-[6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]hexyl]-10H-phenothiazin-2-yl]ethanone in 0.6 mL of tetrahydrofuran is treated with 0.41 mL (0.41 mmol) of 1M tetrabutylammonium fluoride in tetrahydrofuran. The reaction is stirred for 3 hours at room temperature, then diluted with 20 mL of ethyl acetate. The organic layer is washed successively with 10% sodium bisulfate solution and saturated sodium chloride solution, then dried over magnesium sulfate and concentrated in vacuo to give 114 mg of 1-[10-(6-hydroxyhexyl)-10H-phenothiazin-2-yl]ethanone as a dark oil. The 1H NMR (300 MHz, CDCl3) is consistent with the desired product; IR (neat) 3400, 1680, 1590, 1560 cm-1 ; MS m/e calculated for C20H23NO2S: 341.1449, found 341.1456.

Provenance & Evidence