Calcium Carbonate → HCID 54329766, compound

Participants

Reaction Steps

To a suspension of trimethyloxonium tetrafluoroborate (0.44 g, 2.97 mmoles) in dry methylene chloride (15 ml) was added at room temperature the dithialane prepared in 1I (1.45 g, 2.97 mmoles) and the mixture was stirred for 1 hr. Then a 9:1 mixture of acetone and water (5 ml) containing calcium carbonate (0.6 g, 5.94 mmoles) was added and the mixture was stirred overnight at room temperature. The precipitate was filtered off and after dilution with saturated brine the mixture was extacted three times with ether. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to afford an oil. The resulting oil was dissolved in ethanol (10 ml) and sodium borohydride (56 mg, 1.48 mmoles) was added. The mixture was stirred 30 min at 0° C. The excess of sodium boronhydride was reacted with acetone, the mixture was acidified with acetic acid and concentrated under reduced pressure. The residue was taken with water and extracted three times with ether. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to afford an oil. Flash chromatography on silicagel and elution with a 28:72 mixture of ethyl acetate and hexane afforded the title alcohol as an oil (0.813 g, 74%). NMR (H1, CDCl3, 60 MHz) characteristic peaks: 1.06 (s, 9), 3.4 to 3.8 (m, 4), 5.0 (dt, JHF =21 Hz, JHH =8 Hz, 7.2 to 7.76 (m, 10).

Provenance & Evidence