Sodium hydride → HCID 86623857, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-(1,3-dioxolan-2-yl)ethyltriphenylphosphonium bromide (5.0 g, 11.3 mmol) in THF (30 mL) under Ar was added NaH (60% in mineral oil, 0.48 g, 11.3 mmol). The reaction was heated to reflux for 1 h. The resulting orange colored suspension was cooled to 0° C. and 5-fluoro-2-methoxybenzaldehyde (1.54 g, 10.0 mmol) was added and the reaction was stirred for 12 h at room temperature. The mixture was poured to a separatory funnel containing ammonium chloride aqueous solution (sat. NH4Cl/H2O=1:1, v:v, 30 mL). The organics were extracted with EtOAc (3×80 mL) and the combined organic layers were washed with brine (60 mL) and dried over Na2SO4. The solvent was removed in vacuo and product was purified by flash column chromatography (Rf=0.15, EtOAc/Hexane, 7:93, v:v) to result in the product (2.63 g, 66%) as a mixture of cis and trans (cis:trans=4:1): 1H NMR (the major isomer): (CDCl3, 500 MHz): δ 7.08 (dd, J=3.1, 8.7 Hz, 1 H), 6.93 (dt, J=3.1, 8.7 Hz, 1 H), 6.78 (dd, J=4.3, 8.7 Hz, 1 H), 6.63 (d, J=11.9 Hz, 1 H), 5.83 (td, J=7.3 Hz, 11.9 Hz, 1 H), 4.99 (t, J=4.6 Hz, 1 H), 4.02-3.99 (m, 2 H), 3.90-3.87 (m, 2 H), 3.80 (s, 3 H), 2.64-2.62 (m, 2 H).

Provenance & Evidence