4-Toluenesulfonyl chloride → trans-6-Methoxy-1-phenyl-2-(4-methylbenzenesulfonyl)oxy-1,2,3,4-tetrahydronaphthalene

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Reaction Steps

A solution of para-toluenesulfonyl chloride (1.8 g, 9.43 mmol) in dichloromethane (10 mL) was added to a solution of trans-6-methoxy-1-phenyl-1,2,3,4-tetrahydronaphthalen-2-ol 29 (2.0 g, 7.86 mmol), N,N-diisopropylethylamine (4.8 mL, 27.5 mmol) and 4-dimethylaminopyridine (1.15 g, 9.43 mmol) in dichloromethane (40 mL) at 0C. The resultant solution was stirred at ambient temperature for 16 h. The solution was washed successively with 1 N aqueous sodium hydroxide (×2) and a saturated aqueous solution of sodium chloride, then dried over sodium sulfate. The solvent was evaporated in vacuo to give crude trans-6-methoxy-1-phenyl-2-(4-methylbenzenesulfonyl)oxy-1,2,3,4-tetrahydronaphthalene 30 (3.47 g), as a pale yellow solid which was used without further purification in the subsequent step. 1H NMR(CDCl3) δ1.90-2.04 (m, 1H), 2.14-2.24 (m, 1H), 2.42 (s, 3H), 2.83-3.07 (m, 2H), 3.77 (s, 3H), 4.16 (d, 1H), 4.80-4.87 (m, 1H), 6.60-6.67 (m, 3H), 6.82-6.90 (m, 2H), 7.13-7.23 (m, 5H), 7.58 (d, 2H).

Provenance & Evidence