HCID 11243997, compound → HCID 11438532, compound

Participants

Reaction Steps

To a solution of (2R)-2H-chromen-2-ylmethyl 4-methylbenzenesulfonate (1.70 g, 55.00 mmol) in ethanol (100 mL) is added palladium on carbon (10 wt. %, 0.17 g) and the reaction mixture is shaken under an H2 atmosphere (50 psi) for 6 hours. The reaction mixture is filtered (celite) and the solvent removed in vacuo to provide (2R)-3,4-dihydro-2H-chromen-2-ylmethyl 4-methylbenzene-sulfonate (1.62 g, 95%) as a colorless oil which crystallizes upon standing. [α]D25=−52.69 (c 10.06 in methanol, >97% ee); Rf=0.60 (silica, ethyl acetate:hexanes 2:3); Anal. Calcd. for C17H18O4S: C, 64.13; H, 5.70. Found: C, 63.90; H, 5.71.

Provenance & Evidence