HCID 14986530, compound → HCID 14986532, compound

Participants

Reaction Steps

7-Azido-5,6-dihydro-6-hydroxy-5,5-dimethyl-7H-thieno[3,2-b]pyran (2.0 g, 8.88 mmol) Was added carefully in small portions to a mixture of lithium aluminum hydride (0.67 g, 17.8 mmol) in diethyl ether (40ml). The resultant mixture was stirred an additional 1 h at rt and quenched with successive dropwise addition of water (0.7 ml), 15% aqueous sodium hydroxide (0.7 ml) and water (2.0 ml). The aluminum salts were removed by filtration and the ether solution was dried over magnesium sulfate. The solvent was evaporated in vacuo to give the product 1.64 g (93%) as a beige solid; mp 111°-116° C.; IR(KBr):3110, 2971, 1565 and 1403 cm-1 ; MS:m/z 200 (MH+); 1H NMR (CDCl3):δ 1.24(s,3H), 1.48(s,3H), 1.85(bs,3H, exchanges with D2O), 3.38 (d,J=8.6 Hz,1H), 3.70 (d,J=8.6 Hz,1H), 6.55 (d,J=5.4 Hz,1H) and 7.07(d,J=5.4 Hz,1H).

Provenance & Evidence