Sodium hydride → HCID 69051121, compound

Participants

Reaction Steps

To 17-phenylmethyloxy-3,6,9,12,15-pentaoxaheptadecan-1-ol (15) (16.38 g, 43.9 mmol) in dry dimethylformamide (250 ml) was added 8-triphenylmethyloxy-3,6-dioxaoctyl methanesulfonate (13) (28.23 g, 60 mmol, 1.35 eq.) and sodium hydride (4.0 g, 100 mmol, 2.3 eq., 60% w/w in mineral oil). The reaction was left to stir for four days at room temperature after which time it was concentrated in vacuo. The reaction mixture was re-dissolved in diethyl ether (400 ml) and cooled in an ice bath to 0° C. Water was then slowly added until hydrogen was no longer evolved. The organic phase was ten partitioned twice with aq. sat. NaCl with a little NaHCO3 (2×300 ml), dried over anhydrous sodium sulphate and concentrated in vacuo to give a viscous dark brown oil. The product was isolated by N.P.S.G. chromatography, eluting with ethyl acetate only to yield (16) as a yellow oil (24.2 g, 75.0%).

Provenance & Evidence