3,4-dihydro-2H-pyran → 2H-Pyran, 2-[(8-bromooctyl)oxy]tetrahydro-

To a stirred, room temperature suspension of Amberlyst 15 resin (2.37 g) in a solution of 8-bromo-1-octanol (9.50 g, 0.0454 mol) in heptane (95 mL) was added dropwise neat 3,4-dihydro-2H-pyran (5.0 mL, 0.055 mol) under a nitrogen atmosphere, and the mixture was stirred for 22 hours. The resin was filtered off, and the filtrate was rotoevaporated to an oil. The oil was chromatographed on silica gel (400 g, 230-400 mesh) using PET ether-diethyl ether (10:1, 10×500 mL) as eluent. Fractions containing title compound were rotoevaporated and dried in vacuo to give a clear, colorless oil, yield 10.92 g (82%). 1H NMR (CDCl3): δ 4.6 (dd, 1H), 3.9 (m, 1H), 3.8 (m, 1H), 3.5 (m, 1H), 3.4 (m, 3H), 1.8 (m, 3H), 1.7 (m, 1H), 1.6 (m, 6H), 1.4 (m, 1H), 1.3 (m, 7H).

1. filtrationThe resin was filtered off
2. customThe oil was chromatographed on silica gel (400 g, 230-400 mesh)
3. additionFractions containing title compound
4. customdried in vacuo
5. customto give a clear, colorless oil, yield 10.92 g (82%)

ORD record

ord-8aa5257b5a4f46ee90939db0d458e67b

Source dataset

uspto-grants-1994_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05362744