Water → HCID 21078360, compound

Participants

Reaction Conditions

Reaction Steps

1-(1,1-Dimethyl-2-propynyl)-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane (22.6 g) in dry tetrahydrofuran (250 ml) was cooled to −50° C. under an atmosphere of nitrogen with stirring and a solution of n-butyl lithium (44 ml, 2.5M solution in hexanes) was added dropwise over 10 minutes. The mixture was stirred for 0.5 hour, allowed to warm to −20° C. and formaldehyde gas bubbled through the mixture until no starting material remained, as determined by glc analysis. On completion of the reaction, the mixture was treated with water, the ether phase separated, the aqueous phase extracted with ethyl acetate (twice) and the organic extracts combined and washed with water (three times). The combined organic extract was dried over magnesium sulphate and evaporated under reduced pressure to give 4-methyl-4-(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopent-1-yl)pent-2-yn-1-ol (24.96 g) as a pale yellow liquid.

Provenance & Evidence