Tetrahydrofuran → alpha1-Phenyl-1,2-benzenedimethanol

Participants

Reaction Steps

Phtalid was reacted with PhLi (1 eq, 2M in cyklohexane/diethylether 75/25) according to the general procedure. The reaction mixture was then transferred to a slurry of LiAlH4 in THF kept at 0° C. and under N2 -atmosphere. The temperature was raised to RT and the reaction mixture was stirred for 1.5 hour. H2O was added very slowly at 0° C., followed by NaOH (15%) and H2O. CH2Cl2 and MgSO4 was added. The mixture was filtrated with a glass filter funnel and the filtrate was evaporated to give 74% of 12B. 1H-NMR: 7.65-7.15 (m, 9H, Ar--H); 5.99 (s, 1H, CH(Ph)--OH); 4.63 (s, 1H, OH); 4.63 (s, 1H, OH); 4.59 (d, 1H, J=12 Hz, CH2 --OH); 4.42 (d, 1H, J=12 Hz, CH2 --OH);

Provenance & Evidence