Tetrahydrofuran → HCID 20196448, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 5.0 g of methyl triphenylphosphonium bromide in 50 ml of anhydrous tetrahydrofuran and 4.0 ml of hexamethylphosphorous triamide was gradually added 27 ml of 0.5M potassium bis-trimethylsilylamide. The resultant mixture was then stirred at room temperature for 30 minutes, after which time it was cooled to -60° C. (dry ice/acetone bath) and treated dropwise with a solution of 8.0 g (210 mmol) of the compound of Example 2(b) in 50 ml of anhydrous tetrahydrofuran and stirred for 1 hour at -60° C. and for 1 hour at ice bath temperature. The solids were then filtered off and the filtrate evaporated in vacuo to afford an oil. The oil was then chromatographed on silica gel employing a mixture of petroleum ether and methyl-t-butyl ether in a ratio of 9:1 as the eluent to yield a yellow oil.

Provenance & Evidence