Stannous chloride dihydrate → HCID 22989531, compound

Participants

Reaction Steps

(2R)-Toluene-4-sulfonic acid 8-allyl-7-nitro-2,3-dihydro-benzo(1,4)dioxin-2-ylmethyl ester (5.3 g, 13 mmole) and tin (II) chloride dihydrate (14.7 g, 65 mmole) were combined in 500 mL of ethyl acetate and the mixture refluxed for 3 hours under nitrogen. The reaction was allowed to cool to room temperature and was quenched by the addition of 300 mL of saturated aqueous sodium bicarbonate. The biphasic mixture was filtered through celite, the phases separated and the aqueous back-extracted with 200 mL of ethyl acetate. The combined organic phases were washed with 250 mL portions of water and saturated brine, dried over sodium sulfate, filtered and concentrated in vacuum. The residue was column chromatographed on silica gel with methylene chloride as eluant to give 2.2 g of the (R)-enantiomer of the title compound as an orange oil. 1H-NMR (CDCl3): doublet 7.8 δ (2 H); doublet 7.35 δ (2 H); doublet 6.6 δ (1 H); doublet 6.25 δ (1 H); multiplet 5.8 δ (1 H); singlet 5.05 δ(1 H); doublet 5.0 δ (1 H); multiplet 4.4 δ (1 H); multiplet 4.2 δ (3 H); doublet of doublets 4.0 δ (1 H); doublet 3.25 δ (2 H); singlet 2.45 δ (3 H).

Provenance & Evidence