HCID 86586529, compound → HCID 22989532, compound

Participants

Reaction Steps

0.70 g (1.5 mmole) of toluene-4-sulfonic acid (2R)-7-nitro-8-(2-nitro-but-1-enyl)-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester was dissolved in 100 mL of ethyl acetate and 0.10 g of platinum oxide added. The mixure was treated with 45 psi of hydrogen on a Parr hydrogenation apparatus for 5 hours. The mixture was then filtered through celite and concentrated in vacuum. The residue was column chromatographed on silica gel with 1:1 ethyl acetate/hexane to give 0.52 g of the (R)-enantiomer of the title compound as a yellow oil. 1H-NMR (CDCl3): doublet 7.8 δ (2 H); doublet 7.3 δ (2 H); doublet 6.76 δ (1 H); doublet 6.64 δ (1 H); singlet 6.16 δ (1 H); multiplet 4.5 δ (1 H); multiplet 4.3 δ (3 H); quartet 4.1 δ (1 H); quartet 2 H); singlet 2.5 δ (3 H); triplet 1.3 δ (3 H).

Provenance & Evidence