mp 44 5 45 5 u00b0 c u03b1 23 d u2212 22 7 c 2 2 ch 2 cl 2 1 h nmr cdcl 3 300 mhz u03b4 0 92 0 94 d 6h j 6 8 hz 1 79 1 88 m 1h 2 52 2 54 m 2h 3 66 s 3h 3 81 3 86 m 1h 5 10 s 2h 5 15 5 18 m 1h 7 36 7 37 m 5 h 13 c nmr cdcl 3 75 mhz u03b4 18 5 19 3 31 6 36 8 51 7 53 6 66 6 128 0 128 5 136 5 156 0 172 2 ir film cm u2212 1 1239 1531 1731 2961 3338 hrms ei calcd for c 15 h 21 no 4 m 279 1471 found 279 1478 to an ice cooled solution of 4 0 66 g 2 4 mmol in anhydrous thf 10 ml was added dropwise lithium borohydride 2 0 m solution in thf 1 8 ml 3 6 mmol over 5 min a solution of methanol 0 20 ml 4 8 mmol in anhydrous thf 5 ml was then added over 10 min and the mixture was stirred further overnight allowing the temperature to rise to room temperature the solvent was evaporated and the residue was dissolved in ethyl acetate 70 ml washed with hydrochloric acid 1 n 20 ml u00d7 2 saturated sodium bicarbonate 20 ml and brine 20 ml dried with sodium sulfate concentrated and chromatographed etoac hexanes 1 1 to give a white solid 0 42 g 71 as the desired alcohol mp 52.