HCID 11292172, compound → HCID 12051141, compound

Participants

Reaction Steps

[(2R)-7-Oxo-2,3-dihydro-7H-[1,4]dioxino[2,3-h]chromen-2-yl]methyl 4-methylbenzenesulfonate (1.0 g, 2.6 mmole) dissolved in acetic acid (50 mL) was hydrogenated at 40 psi in the presence of 0.30 g platinum oxide on a Parr shaker for 5 hours. The catalyst was filtered through celite and the filter cake washed with water. The filtrate was then extracted with ethyl acetate and the organic layer was washed with saturated sodium bicarbonate until neutral. The organic extracts were dried over magnesium sulfate, filtered and evaporated to give 0.78 g (81%) of the (R)-enantiomer of the title compound as a clear oil. 1H (CDCl3) doublet 7.8 δ (2 H); doublet 7.4 δ (2 H); singlet 6.5 δ (1 H); singlet 6.4 δ (1 H); multiplet 4.2 δ (1 H); multiplet 4.1-4.3 δ (5 H); multiplet 4.0 δ (1 H); triplet 2.7 δ (2 H); singlet 2.4 δ (3 H); triplet 2.0 δ (2 H).

Provenance & Evidence