Thiophenol → HCID 13714036, compound

Participants

Reaction Conditions

Reaction Steps

In a microwave reaction tube, a mixture of 5-methoxy-3,3-dimethyl-indan-1-one (880 mg, 4.63 mmol), benzenethiol (510 mg, 4.63 mmol), and potassium carbonate (64 mg, 0.46 mmol) in NMP (5 mL) is purged with N2. The reaction mixture is heated at 220° C. for 30 min under microwave irradiation. The reaction mixture made to alkaline with 1N aqueous NaOH (10 mL) and extracted with Et2O (3×20 mL). The aqueous part is acidified in an ice bath with 6N HCl and extracted with Et2O (3×20 mL). The combined organic phases are washed with brine and dried over Na2SO4. After concentration, the crude product is purified with silica gel column chromatography (30% ethyl acetate in hexanes) to afford 5-hydroxy-3,3-dimethyl-indan-1-one as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 7.63 (d, 1H, J=8 Hz), 6.88 (d, 1H, J=2 Hz), 6.84 (dd, 1H, J=2, 8 Hz), 6.14 (s, 1H), 2.59 (s, 2H), 1.40 (s, 6H), ESMS m/z 177.1 (M+H+).

Provenance & Evidence