1: 65percent aq. acetic acid / tetrahydrofuran / 2 h / 50 °C 2: 90 percent / imidazole / dimethylformamide / 1 h / 23 °C 3: 95 percent / H2 / napthalene*Cr(CO)3 / tetrahydrofuran / 23 h / 45 °C / 55163.1 Torr 4: 100 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 13 h / 23 °C 5: 100 percent / 10percent aq. NaOH / methanol / 13 h / 0 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11343078', constants.ctx, '0')">sodium tetrahydroborate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098229', constants.ctx, '0')">methanol</a> <br />T=-25&deg;C;&nbsp;0.666667&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 1) NaH / 1) THF, 23 deg C, 30 min, 2) THF, 23 deg C, 40 min<br />2: 81 mg / NaBH₄ / methanol / 0.67 h / -25 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: SO₃*pyridine, triethylamine / dimethylsulfoxide / 0.5 h / 23 &deg;C<br />2: 1) NaH / 1) THF, 23 deg C, 30 min, 2) THF, 23 deg C, 40 min<br />3: 81 mg / NaBH₄ / methanol / 0.67 h / -25 &deg;C<br /> <br /> &nbsp;