反应详情

A suspension of (S)-1-(1-chloro-3-methylnaphthalen-2-yl)ethane-1,2-diol (6.70 grams, 28.2 mmol) and CH2Cl2 (67 mL) was treated with pyridine (4.78 mL, 59.2 mmol) at 23° C. Trityl chloride (8.28 g, 29.6 mmol) was added and the reaction was stirred for 24 h. The reaction was washed with 1.0 M aq CuSO4 monohydrate (3×50 mL), H2O (2×50 mL), and brine (50 mL). The final organic layer was dried over Na2SO4, filtered, and concentrated. The residue was treated with benzene and purified by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes) to give (S)-1-(1-chloro-3-methylnaphthalen-2-yl)-2-(trityloxy)ethanol. 1H NMR (400 MHz, CDCl3) δ 8.22 (d, J=8.2 Hz, 1H), 7.69 (d, J=8.2 Hz, 1H), 7.53-7.44 (m, 2H), 7.51 (s, 1H), 7.43-7.40 (m, 6H), 7.30-7.20 (m, 9H), 5.93-5.77 (m, broad, 1H), 3.59 (dd, J=9.4, 9.0 Hz, 1H), 3.52 (dd, J=9.4, 5.0 Hz, 1H), 2.85 (d, broad, J=4.3 Hz, 1H), 2.52 (s, 3H).

1. washThe reaction was washed with 1.0 M aq CuSO4 monohydrate (3×50 mL), H2O (2×50 mL), and brine (50 mL)
2. dry with materialThe final organic layer was dried over Na2SO4
3. filtrationfiltered
4. concentrationconcentrated
5. additionThe residue was treated with benzene
6. custompurified by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes)