Triphenylphosphine → HCID 58400533, compound

Participants

Reaction Conditions

Reaction Steps

On a stirred solution composed by 2-bromo-4-fluoro-phenol (12.07 g, 0.063 mol) and triphenylphosphine (16.18 g, 0.063 mol) in THF (85 ml) under nitrogen at 18° C., 1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-prop-2-en-1-ol (10.0 g, 0.054 mol) was added as a crude product. The reaction mixture was then cooled to 0° C. and diisopropyl-aza-dicarboxylate (12.78 g, 0.063 mol) was added dropwise over a period of 30 min. At the end of the addition the temperature was raised gradually to 18° C. and the mixture left to stir for further 1 h. The crude reaction was then concentrated under reduced pressure and then MTBE (31 g) added. After 15 min agitation, the slurry was filtered and the panel washed with MTBE (2×10 g). The mother liquors were then concentrated in vacuo and heptane (23 g) added. After 30 min stirring, the slurry was filtered and the cake washed with heptane (11 g). The mother liquors were then concentrated in vacuo and purified by column chomatography on silica using a mixture heptan:ethyl acetate:triethylamine 9.5:0.5:0.01, as eluent. 14.28 g of (R)-4-(1-(2-bromo-4-fluorophenoxy)allyl)-2,2-dimethyl-1,3-dioxolane were isolated as a mixture of diastereoisomers (80% yield).

Provenance & Evidence