Ethanol → HCID 21314007, compound

Participants

Reaction Steps

Crude 5-(oxoacetyl)-2-(phenylmethoxy)benzoic acid, methyl ester, hydrate (prepared in 15b above) in ethanol (100 ml) was treated with 4-(4-fluorophenyl)-2-methyl-2-butanamine (generated from its hydrochloride salt (1.5 g) prepared in (c) above). The solution was boiled for 30 min. and then evaporated to leave a yellow gum. The gum in dry tetrahydrofuran (50 ml) was dripped into a stirred solution of lithium aluminium hydride (1.0 g) in dry tetrahydrofuran (50 ml) at room temperature. The mixture was stirred for 20 hr. then boiled for 2 hr. Water (5 ml) was slowly added, the mixture was filtered and the filtrate was evaporated to leave a colourless gum which crystallised from ether-light petroleum (b.p. 60°-80°) as colourless needles, m.p. 76°-79° (0.37 g).

Provenance & Evidence