[Cl:1][CH2:2][CH2:3][C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([OH:7])[CH:5]=[CH2:6].B.C1C[O:18]CC1.[OH-].[Na+].OO>C1COCC1>[Cl:1][CH2:2][CH2:3][C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([OH:7])[CH2:5][CH2:6][OH:18]
To a 0° C. solution of 5-chloro-3-phenylpent-1-en-3-ol (6.12 g, 31.12 mmol) in 125 mL THF was added a 1M solution of BH3.THF (62.2 mL, 62.2 mmol) dropwise. The reaction mixture was stirred for 3 h at 0° C., and 5M NaOH (38 mL, 190 mmol) was slowly added, followed by 30% H2O2 (56 mL, 495 mmol). After stirring for 90 min at room temperature, the organic layer was isolated and the aqueous layer extracted with EtOAc. The organic layers were pooled, washed with saturated aqueous Na2S2O3 and saturated aqueous NH4Cl, dried (Na2SO4), filtered, and passed through a silica plug to provide 5-chloro-3-phenylpentane-1,3-diol (4.3 g, 64%) as an oil. 1H NMR (400 MHz, CDCl3): δ 7.43-7.34 (m, 5H), 7.27 (m, 1H), 3.80 (td, 1H, J=10.8, 4.2 Hz), 3.67-3.52 (m, 2H), 3.22 (td, 1H, J=10.5, 5.1 Hz), 2.38 (ddd, 1H, J=13.7, 10.3, 5.9 Hz), 2.28 (ddd, 1H, J=13.7, 10.4, 5.1 Hz), 2.23 (m, 1H), 2.03 (ddd, 1H, J=14.8, 4.6, 2.9 Hz).
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