3,4-dihydro-2H-pyran → 2-(6-Bromo-2,2-dimethylhexyloxy)-tetrahydropyran

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Reaction Steps

According to the procedure for the preparation of 207d, (Ackerley, N. et al. J. Med. Chem. 1995, 38, 1608-1628; Manley, P. W. et al. J. Med. Chem. 1987, 30, 1812-1818) 206c (521.0 g, 2.49 mol) was reacted with 3,4-dihydro-2H-pyran (278.0 g, 3.30 mol) and p-toluenesulfonic acid hydrate (3.13 g, 16 mmol) in CH2Cl2 (2.2 L) to yield 207c (603.0 g, 83%) as a pale-yellow oil, which was used without further purification. 1H NMR (CDCl3): δ 4.55 (t, 1 H, J=3.3), 3.84 (m, 1 H), 3.50 (m, 1 H), 3.47 (d, 1 H, J=9.0), 3.42 (t, 2 H, J=6.7), 2.99 (d, 1 H, J=9.0), 1.88 (m, 2 H), 1.75-1.33 (m, 10 H), 0.91 (s, 3 H), 0.90 (s, 3 H). 13C NMR (CDCl3): δ 99.37, 76.58, 62.17, 38.56, 34.43, 34.19, 33.90, 30.88, 25.79, 24.80, 24.71, 22.89, 19.67. HRMS (LSIMS, nba): Calcd for C13H25BrO2 (MH+): 293.1116, found: 293.1128.

Provenance & Evidence