Sulfuric Acid → t-Butyl fur-2-ylglyoxylate

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Reaction Steps

Fur-2-ylglyoxylic acid (12.5g) and liquid isobutylene (ca 25 ml) were added to a cooled stirred solution of sulphuric acid (10 ml) in anhydrous ether (100 ml) and the solution was kept at 3° C for 3 days. Ether (150 ml) was added, the solution washed with aqueous sodium bicarbonate solution until free from acid, dried over sodium sulphate and evaporated, giving a brown oil. The oil was distilled at 76°-82° C/0.3 mm, giving t-butyl fur-2-ylglyoxylate (11.6g) λmax (EtOH) 233 (ε2,080) and 286 nm (ε11,700), νmax (CHBr3) 1718 (CO2But) and 1664 cm-1 (=C-CO-), τ (DMSO.d 6; 60 MHz) 1.80, 2,32, 3.15 (furyl protons) and 8.41 (But).

Provenance & Evidence