Sodium hydride → Methyl 8-t-butyldimethylsilyloxy-8-(2-naphthyl)-2-octenoate

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Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (60% in mineral oil, 177 mg, 4.42 mmol) in THF (25 mL) at room temperature under nitrogen atmosphere was added dropwise neat methyl diethylphosphonoacetate (811 μL, 4.42 mmol). The resulting solution was stirred for 10 minutes while cooling down to 0° C. A solution of crude aldehyde 183 (1.05 g, 2.94 mmol) in THF (10 mL) was transferred via cannula. The resulting solution was stirred for 15 minutes at 0° C. and quenched with a saturated aqueous solution of ammonium chloride. The THF was evaporated in vacuo and the aqueous residue was partitioned between diethyl ether and water. The aqueous layer was extracted with diethyl ether and the combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo. The crude residue was purified by flash chromatography (5% ethyl acetate/hexane), affording the title compound 184 in 63% yield (1.30 g). 1H NMR: (300 MHz, CDCl3) δ: 7.83-7.78 (m, 3H), 7.69 (s, 1H), 7.49-7.41 (m, 3H), 6.94 (dt, J=15.4, 7.1 Hz, 1H), 5.79 (dt, J=15.7, 1.1 Hz, 1H), 4.79 (dd, J=7.1, 5.2 Hz, 1H), 3.71 (s, 3H), 2.16 (q, J=7.4 Hz, 2H), 1.81-1.62 (m, 2H), 1.48-1.29 (m, 4H), 0.90 (s, 9H), 0.04 (s, 3H), −0.15 (s, 3H). MS (ESI)=413 (MH+).

Provenance & Evidence