Tetrahydrofuran → HCID 178490597, compound

Participants

Reaction Steps

Trans-4-(4-methoxyphenyl)cyclohexanecarbaldehyde (774 mg, 3.55 mmol) was dissolved in tetrahydrofuran (7.2 ml) and t-BuOH (18 ml) was added followed by 2-methyl-2-butene (7.2 ml, 68.0 mmol). To this solution was added sodium dihydrogen phosphate, hydrate (1072 mg, 7.80 mmol) as a solution in water (4.1 mL). Finally, sodium chlorite (882 mg, 7.80 mmol) was added as a solution in water (4.1 mL). The reaction was stirred at room temperature for 2 hours and then diluted with EtOAc (100 mL) and washed with water (25 mL) and brine (25 mL). The aqueous washes were combined, acidified with 1N HCl and extracted with EtOAc (50 mL). The two EtOAc extracts (before and after acidification) were combined, dried over Na2SO4, filtered, and concentrated. The residue was taken up in toluene (20 ml) and MeOH (3 ml). TMS-diazomethane (2.82 ml, 5.64 mmol) was added dropwise. Evolution of gas was observed, and a yellow color persisted. After 45 minutes, the reaction was quenched with HOAc, diluted with EtOAc (75 mL), and washed with saturated NaHCO3 and brine (20 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel with 0 to 40% EtOAc/hexanes afforded methyl trans-4-(4-methoxyphenyl)cyclohexanecarboxylate. 1H NMR (CDCl3, 500 MHz) δ 7.12 (d, J=8.7 Hz, 2H), 6.84 (d, J=8.5 Hz, 2H), 3.79 (s, 3H), 3.69 (s, 3H), 2.47 (m 1H), 2.35 (m, 1H), 1.92-2.12 (m, 4H), 1.53-1.63 (m, 2H), 1.40-1.49 (m, 2H).

Provenance & Evidence