[CH2:1]([OH:4])[C:2]#[CH:3].[Br:5][CH2:6][CH2:7][CH2:8][CH2:9]Br.[OH-].[Na+]>O>[Br:5][CH2:6][CH2:7][CH2:8][CH2:9][O:4][CH2:1][C:2]#[CH:3]A mixture of 2-propyn-1-ol (10 g), 1,4-dibromobutane (60 ml), 50% aqueous sodium hydroxide (60 ml) and TAB (2 g) was stirred vigorously overnight. Water (250 ml) was added and the mixture was extracted with ether (2×200 ml). The organic extracts were dried and concentrated to a yellow oil which was purified by FCC (hexane→System D 19:1) to give the title compound as a colourless oil (19.7 g). T.l.c. (System D 19:1) Rf 0.37.
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