Diisobutylaluminum hydride → HCID 53822047, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(3-benzyloxy-4-propoxy-5-propylsulfonylphenyl) butyrolactone (6.90 g, 0.015 mol) in dry toluene (65 ml) at −78° C. was added 0.9 M toluene solution of DIBAL-H (3.40 g, 26.61 ml) dropwise at −78° C. and stirred for 1 h. Upon completion, the reaction was quenched by adding methanol (7 ml) at −78° C. The mixture was warmed to −20° C. followed by the addition of saturated sodium potassium tartarate solution while maintaining the temperature between −10° C. and 0° C. The mixture was stirred at 0° C. for 1 h. Then the two phases were separated, the aqueous layer was extracted with ethyl acetate and the combined organic layer was washed with water followed by brine, dried (Na2SO4), filtered and concentrated. The crude 2-hydroxy-5-(3-benzyloxy-4-propoxy-5-propylsulfonylphenyl) tetrahydrofuran (6.86 g) was used for the next step without further purification (99%). TLC: Acetone:benzene (1:9), Rf=0.33; 1H NMR(CDCl3, 200 MHz): δ 1.03 (m, 6H), 1.65-2.15 (m, 7H), 2.3-2.6 (m, 1H), 3.35 (m, 2H ), 4.15 (t, J=6.45 Hz, 2H), 4.98 (apparent t, J=6.97 Hz, 0.5H), 5.18 (t, J=6.51 Hz, 0.5H), 5.15 (2s, 2H), 5.6, 5.75 (brs, 1H), 7.1-7.22 (m, 1H), 7.3-7.48 (m, 6H). FAB Mass: 434 (M+).

Provenance & Evidence