Water → HCID 54526121, compound

Participants

Reaction Steps

trans-2-(3-Tetrahydropyranyloxy-but-1-ynyl)-5-(4-fluorophenyl)tetrahydrofuran (204, 280 mg, 0.9 mmol) was dissolved in methanol (15 mL). To this solution was added p-toluenesulfonic acid (50 mg) and the resulting solution was stirred for 45 minutes. Saturated sodium bicarbonate solution (10 mL) was added. After 5 minutes of stirring, the solution was added to 10 mL of water, diluted with 15 mL of brine and extracted with methylene chloride (3×30 nL). The combined organics were dried over sodium sulfate and the solvent was removed via rotary evaporator to yield 212 mg (100%) of trans-2-(3-hydroxy-but-1-ynyl)-5-(4-fluorophenyl) tetrahydrofuran (205). 1H-NMR (CDCl3) 6 7.29 (2H, dd, J=8.7, 5.2 Hz), 7.01 (2H, t, J=8.7 Hz), 5.09 (1H, t, J=7.4 Hz), 4.92 (1H, t, J=7.4 Hz), 4.59 (1H, q, J=6.6 Hz), 2.30-2.50 (2H, in), 2.05-2.15 (1H, m), 2.00 (1H, br s), 1.75-1.88 (1H, m), 1.47 (3H, d, J=6.6 Hz).

Provenance & Evidence