Hydrochloric Acid → HCID 178490595, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of (methoxymethyl)triphenylphosphonium chloride (4632 mg, 13.51 mmol) in THF (60 mL) was cooled to 0° C. Potassium hexamethyldisilazide (22.52 ml, 11.26 mmol) was added dropwise via syringe and the solution turned dark red. After the reaction was stirred at 0° C. for 15 minutes, 4-(4-methoxyphenyl)cyclohexanone (920 mg, 4.50 mmol) was added as a solution in THF (15 mL). The reaction was warmed to r.t. and stirred at r.t. for 2 hours. Next, 5 mL of concentrated HCl was added to 10 mL of water and this solution was added to the reaction dropwise via addition funnel. The reaction was allowed to stir for 16 hours at room temperature. The reaction was then diluted with EtOAc (150 mL). The organic layer was washed with H2O (3×50 mL), saturated NaHCO3 (50 mL), and brine (50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel with 0 to 50% EtOAc/hexanes and isolation of the major product afforded trans-4-(4-methoxyphenyl)cyclohexanecarbaldehyde. 1H NMR (CDCl3, 500 MHz) δ 9.67 (s, 1H), 7.12 (d, J=8.4 Hz, 2H), 6.85 (d, J=8.7 Hz, 2H), 3.79 (s, 3H), 2.45 (m, 1H), 2.27 (m, 1H), 1.98-2.14 (m, 4H), 1.36-1.53 (m, 4H).

Provenance & Evidence