C[O:2][C:3](=O)[C@@H:4]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1)[O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[H-]>CCOCC.C1(C)C=CC=CC=1>[Cl:19][C:15]1[CH:14]=[C:13]([C@@H:4]([O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:7])[CH3:8])[CH:3]=[O:2])[CH:18]=[CH:17][CH:16]=1To a stirred solution of (R)-(3-chloro-phenyl)-(tert-butyl-dimethyl-silanoxy)-acetic acid methyl ester (4.0 g) in anhydrous ether (10 ml) and maintained at <-65° was added dropwise a 1.5M solution of di-isobututylaluminium hydride in toluene (10 ml). When addition was complete the solution was stirred at -65° for a further hour, then quenched with methanol (10 ml). The mixture was allowed to attain room temperature when silica (20 g) was added. Solvent was removed under reduced pressure, and the residue was purified by flash chromatography, eluting with cyclohexane:ethyl acetate (9:1) to give the title compound as a colourless liquid (3.1 g).
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