Bexarotene → {4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-phenyl}-methanol

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Reaction Steps

To a solution of 4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzoic acid in 10 mL of THF was added 300 mg of LiAlH4 at 0° C. The mixture was stirred at room temperature overnight. The excess LiAlH4 was quenched with EtOAc (3 mL). The mixture was stirred for 30 min. 1N HCl was added. A sequence of extraction with EtOAc, filtering, concentration in vacuo and column chromatography yielded 180 mg of the desired alcohol and 103 mg of its acetate. The acetate formed was dissolved in 2 mL of THF, 1 mL of MeOH and 1 mL of H2O. NaOH (0.2 mL of a 1N solution, 0.2 mmol) was added. The mixture was stirred at room temperature for 1 hour. NH4Cl solution was added, and the alcohol product was extracted with EtOAc. After drying over MgSO4, filtering, concentration in vacuo and chromatography, 73.5 mg of the alcohol product was obtained. Total yield of the alcohol was therefore 253.5 mg.

Provenance & Evidence