Potassium Carbonate → HCID 69935910, compound

Participants

Reaction Steps

A solution of the 4-[(3-hydroxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbonyl]benzoic acid methyl ester (from Example 7; 225 mg, 0.61 mmol) in acetone (3 mL) was stirred with K2CO3 (1.0 mmol) at room temperature for one hour. The yellow solution was treated with a solution of 4-t-butylbenzylbromide (168 mg, 0.74 mmol) and allowed to stir for 10 h. The reaction was quenched with saturated aqueous NH4Cl. The aqueous solution was extracted 3 times with EtOAc; the organic layers were combined, and washed with water (2×) and brine. The organic solution was dried (NaSO4), filtered, and concentrated. Purification by cyrstallization (CH2Cl2/hexanes) gave 4-[(3-(4-t-butylbenzyloxy)-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbonyl]benzoic acid methyl ester 298 mg (95%) as a white solid: mp 168-169.5° C; 1H NMR (400 MHz, CDCl3) δ 8.04 (1/2ABq, J=8.5 Hz, 2H, ArH), 7.81 (1/2ABq, J=8.5 Hz, 2H, ArH), 7.44 (s, 1H, ArH), 7.19 (1/2ABq, J=8.2 Hz, 2H, ArH), 6.89 (s, 1H, ArH), 6.87 (1/2ABq, J=8.4 Hz, 2H, ArH), 4.89 (s, 2H, OCH2), 3.94 (s, 3H, OCH3), 1.69 (m, 4H, 2CH2), 1.28 (s, 6H, 2CH3), 1.26 (s, 6H, 2CH3), 1.25 (s, 9H, 3CH3).

Provenance & Evidence