3,4-dihydro-2H-pyran → 2-(6-Bromo-2-methyl-2-p-tolylhexyloxy)-tetrahydropyran

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Reaction Steps

According to the method described for the synthesis of 207d, 206e (18.2 g, 63.8 mmol) was reacted with 3,4-dihydro-2H-pyran (6.4 g, 76.0 mmol) and p-toluenesulfonic acid hydrate (0.43 g, 2.3 mmol) in CH2Cl2 (300 mL) to give 207e (22.0 g, 93%) as an oil, which was used without further purification. 1H NMR (CDCl3): δ 7.25-7.05 (m, 4 H), 4.60-4.48 (m, 1 H), 3.82 (m, 2 H), 3.48-3.37 (m, 2 H), 3.35-3.26 (m, 2 H), 2.30 (s, 3 H), 1.90-1.40 (m, 11 H), 1.34 (s, 3 H), 1.40-1.08 (m, 1 H). 13C NMR (CDCl3): δ 142.78, 135.22, 128.81, 126.39, 99.09, 99.01, 61.93, 61.85, 41.67, 41.56, 38.12, 37.87, 33.68, 33.64, 30.62, 25.96, 22.89, 20.97, 19.41, 19.37. HRMS (LSIMS, nba): Calcd for C19H30O2Br (MH+): 369.1429, found: 369.1451.

Provenance & Evidence