4-Toluenesulfonyl chloride → (+/-)-3-[4-(benzyloxy)-6-chloro-2,3-dihydro-1H-inden-5-yl]-2-hydroxypropyl 4-methylbenzenesulfonate

Participants

Reaction Steps

Treatment of (±)-3-[4-(benzyloxy)-6-chloro-2,3-dihydro-1H-inden-5-yl]propane-1,2-diol (5.60 g, 0.0168 mol) with p-toluenesulfonyl chloride (3.70 g, 0.0194 mol) in pyridine (200 mL) generally according to the procedure described for Intermediate 18 provided 6.30 g (77%) of (±)-3-[4-(benzyloxy)-6-chloro-2,3-dihydro-1H-inden-5-yl]-2-hydroxypropyl 4-methylbenzenesulfonate as a light yellow oil. 1H NMR (DMSO-d6) 8H 7.65(d, 2H); 7.40(m, 7H); 7.05(s, 1H); 5.25(s, 1H); 4.90(s, 2H); 3.80(m, 3H); 2.90(m, 2H); 2.80(m, 3H); 2.65(dd, 1H); 2.40(s, 3H); 2.00(m, 2H).

Provenance & Evidence