Methanol → 3-(3-{2-[3-(3-Hydroxy-2,2-dimethylpropyl)-phenyl]-[1,3]dithian-2-yl}-phenyl)-2,2-dimethylpropan-1-ol

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Reaction Steps

To a suspension of LiBH4 (0.78 g, 33 mmol) in dichloromethane (55 mL) was added methanol (1.04 g, 33 mmol) at rt. After the addition of 3-(3-{2-[3-(2-ethoxycarbonyl-2-methyl-propyl)-phenyl]-[1,3]dithian-2-yl }-phenyl)-2,2-dimethyl-propanoic acid ethyl ester (6.5 g, 12.2 mmol), the reaction mixture was heated to reflux for 6 h. After cooling to rt, saturated ammonium chloride solution (20 mL) and dichloromethane (15 mL) were added. The layers were separated and the aqueous layer was extracted with dichloromethane (2×10 mL). The combined organic phases were dried over sodium sulfate and concentrated in vacuo to afford crude 3-(3-{2-[3-(3-hydroxy-2,2-dimethyl-propyl)-phenyl]-[1,3]dithian-2-yl}-phenyl)-2,2-dimethyl-propan-1-ol (4.66g, 85%) as an oil. 1H NMR (300 MHz, CDCl3): δ (ppm): 7.6-6.8 (m, 8H), 3.63 (s, 4H), 3.16 (s, 4H), 2.95-2.60 (m, 4H), 2.0-1.8 (m, 2H), 1.61 (s, 2H), 0.75 (s, 12H). 13C NMR (75 MHz, CDCl3): δ (ppm): 142.4, 139.2, 131.7, 128.9, 128.1, 127.0, 71.1, 44.9, 43.7, 36.7, 29.6, 27.3, 24.2.

Provenance & Evidence