HCID 11016191, compound → (2S)-1,1,2-Triphenyl-1,2-ethanediol

Participants

Reaction Conditions

Reaction Steps

Lithium aluminium hydnde (1.325 g, 35.0 mmol, 7.0 equiv) is added portionwise to a refluxing solution of (1S)-2,2,1-triphenyl-2-hydroxyethyl (3S,E)-4,4-dimethyl-5-ethyl-3-hydroxy-5-heptenoate 26 (2.364 g, 5.0 mmol) in diethyl ether (50 ml) within a period of 2 h. Refluxing is continued for 30 min. After cooling to 0° C., the reaction is quenched dropwise with 1.35 ml water and 1.35 ml of aqueous NaOH (15%). Diethyl ether (40 ml) and water (2.0 ml) is added. The mixture is stirred for 1 h at r.t. until a white precipitate forms which is filtered off by suction through a small plug of celite. The precipitate is washed with diethyl ether (4×40 ml). The filtrate and the washings are combined and concentrated in vacua. Purification of the residue by flash column chromatography (pentane/diethyl ether 2:1) affords (S)-2,2,1-Triphenyl-ethane-1,2-diol (922 mg, 99%) as a colourless, crystalline solid and (S)-(E)-4,4-Dimethyl-5-ethyl-5-heptene-1,3-diol 28 (836 mg, 90%) as a colourless oil. 13C-NMR (100 MHz, CDCl3): δ=146.2; 121.1; 75.8; 62.6; 44.4; 32.7; 22.8; 21.1; 20.1; 14.3; 13.6

Provenance & Evidence