5,6-Dihydro-2H-pyran-3-carbaldehyde → 5-{4-[(Phenylmethyl)oxy]-1-buten-1-yl]-3,6-dihydro-2H-pyran

Participants

Reaction Conditions

Reaction Steps

To a suspension of (3-benzyloxypropyl)triphenylphosphonium bromide (9.90 g) in dry tetrahydrofuran (30.5 ml) at −15° C. was added butyllithium (8.06 ml, 2.5M in hexanes) dropwise to give a dark orange solution. The reaction temperature was increased to 0° C. and stirring was continued for 30 minutes. A solution of 5,6-dihydro-2H-pyran-3-carbaldehyde (2.26 g) in dry tetrahydrofuran (3 ml) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was filtered through celite and washed with diethyl ether. The filtrate was concentrated in vacuo to give an orange oil. The product was purified by silica chromatography using a gradient elution of 0-25% ethyl acetate/cyclohexane to afford the title compound as a colourless oil (2.04 g).

Provenance & Evidence