[Br-].[OH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[Br:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]O.O>ClCCl.O1CCCC1>[Br:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH:45]=[CH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][OH:2]
A solution of (6-hydroxyhexyl)triphenylphosphonium bromide (5.0 g) in dichloromethane (20 ml) was added dropwise to a mixture of potassium tertiary-butoxide (2.8 g) in tetrahydrofuran (100 ml) at 5°. After ten minutes, 11-bromoundecanol (2.8 g) in tetrahydrofuran (20 ml) was added and the reaction stirred at 5° until TLC indicated completion of the reaction. Water (20 ml) was added and the mixture then concentrated in vacuo. Water (20 ml) was added to the residue and the aqueous phase extracted with ether (2×50 ml). The combined organic extracts were dried (MgSO4) and concentrated in vacuo to give a brown oil. This was subjected to column chromatography to yield 17-bromoheptadec-6-en-1-ol (1.7 g, 45%).
Loading…
