Potassium Carbonate → HCID 57871402, compound

Participants

Reaction Conditions

Reaction Steps

Add 4-bromo-2,2-dimethylhexane-3-one (660 mg, 3.187 mmol) to a mixture of 6-[1-ethyl-1-(4-hydroxy-3-methylphenyl)propyl]naphthalene-2-carboxylic acid methyl ester (1.1 g, 3.035 mmol), and K2CO3 (629 mg, 4.55 mmol) in DMF (10 ml). Maintain the reaction mixture 45° C. for 14 h. Add an additional amount of 4-bromo-2,2-dimethylhexane-3-one (314 mg, 1.52 mmol) and maintain the mixture at 60° C. while stirring for 62 h. Cool the reaction mixture and dilute it with CH2Cl2, filter, and concentrate in vacuo. Chromatograph the resulting residue (CH2Cl2to 1% EtOAc/CH2Cl2) to give the title compound as a colorless viscous oil (1.299 g, 88%). 1NMR (400 MHz, CDCl3) δ ppm: 0.62 (t, J=7.2 Hz, 6H), 1.01 (t, J=7.6 Hz, 3H), 1.16 (s, 9H), 1.88 (m, 2H), 2.16 (m, 4H), 2.19 (s, 3H), 3.97 (s, 3H), 4.86 (dd, J=5.2, 1.6 Hz, 1H), 6.53 (d, J=8.4 Hz, 1H), 6.88 (m, 2H), 7.14 (dd, J=7.2, 1.6 Hz, 1H), 7.73 (d, J=8.8 Hz, 1H), 7.82 (s, 1H), 7.85 (d, J=8.8 Hz, 1H), 8.04 (dd, J=6.4, 2.0 Hz, 1H), 8.52 (s, 1H). High Res. ES-MS: 511.2824; calc. for C32H40O4+Na: 511.2825.

Provenance & Evidence