2-Hydroxymethyl-3-(5-carboethoxypentyloxy)-6-(trimethylacetoxymethyl)-4-pyrone → 2-Formyl-3-(5-carboethoxypentyloxy)-6-(trimethylacetoxymethyl)-4-pyrone

Participants

Reaction Steps

To a solution of 2.3 g of 2-hydroxymethyl-3-(5-carboethoxypentyloxy)-6-(trimethylacetoxymethyl)-4-pyrone in 75 ml of acetone was added 4 g of activated manganese dioxide. The resulting suspension was stirred for 3 hr, at which time the mixture was filtered and the filtrate evaporated to an oil. The oil was chromatographed on silica gel to give the oily aldehyde, 2-formyl-3-(5-carboethoxypentyloxy)-6-(trimethylacetoxymethyl)-4-pyrone weighing 1.6 g (70%). NMR (CDCl3): δ1.28 (3H, t, J = 7 Hz), 1.30 (9H, s), 2.31 (2H, t, J = 5.5 Hz), 4.17 (2H, q, J = 7 Hz), 4.48 (2H, t, J = 7Hz).

Provenance & Evidence