Aluminium lithium hydride → (S)-(4-chloro-2-(pent-4-en-2-yloxy)phenyl)methanol
Reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6](OC(CC=C)C)=[O:7])=[C:4]([O:16][C@H:17]([CH2:19][CH:20]=[CH2:21])[CH3:18])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][OH:7])=[C:4]([O:16][C@H:17]([CH2:19][CH:20]=[CH2:21])[CH3:18])[CH:3]=1Participants
4
Procedure
To a solution of pent-4-en-2-yl 4-chloro-2-((S)-pent-4-en-2-yloxy)benzoate (1.36 g, 4.40 mmol) in THF (15 ml) that was cooled to 0° C. was added dropwise over 30 min lithium aluminum hydride (2.64 ml, 5.28 mmol) and the resulting mixture was stirred at rt. After 3 h, the mixture was cooled to 0° C. and quenched by dropwise addition of brine. The mixture was diluted with EtOAc and the organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. The oil was purified by flash chromatography (Biotage; 0%-50% EtOAc/hexane; 10 CV) to give (S)-(4-chloro-2-(pent-4-en-2-yloxy)phenyl)methanol (0.9554 g, 4.21 mmol, 96% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.21 (d, J=7.8 Hz, 1H), 6.98-6.88 (m, 1H), 6.88 (d, J=1.7 Hz, 1H), 5.86 (ddt, J=17.1, 10.1, 7.1 Hz, 1H), 5.25-5.06 (m, 2H), 4.75-4.62 (m, 1H), 4.62-4.43 (m, 2H), 2.61-2.40 (m, 2H), 2.34 (t, J=6.5 Hz, 1H), 1.38 (d, J=6.1 Hz, 3H).