Dimethyl Sulfoxide → HCID 22392106, compound

In a 250 ml flask equipped with a magnetical stirrer and reflux condenser were placed 6-bromo-1(tetrahydropyranyloxy)-2,2-dimethylhexane (10 g, 0.034 mol) and DMSO (50 ml), then the mixture was treated with K2CO3 (10 g 0.068 mol) in water (100 ml). The reaction mixture was heated under reflux for two days, then was allowed to cool to room temperature and quenched with water (150 ml). The solution was adjusted to pH 7 with 1M HCl and extracted with ether (3×100 ml). The organic layers combined were then washed with saturated NH4Cl (150 ml) and brine (150 ml), dried (MgSO4), and the solvent was removed under reduced pressure, to provide 6.63 g of the above-titled compound as a colorless liquid (85% yield). 1H NMR CDCl3, δ (ppm): 4.40-4.50 (m, 1H), 3.90-3.75 (m, 1H), 3.38 (t, J=6.8 Hz, 1H), 2.97 (d, J=9.3 Hz, 1H), 2.50 (brs, 1H, OH), 1.90-1.20 (m, 12H), 0.84 (s, 3H), 0.86 (s, 3H); 13C NMR CDCl3, δ (ppm): 99.0, 76.2, 62.3, 61.8, 38.8, 34.0, 33.4, 30.5, 25.4, 24.4, 24.3, 19.9, 19.3.

1. customIn a 250 ml flask equipped with a magnetical stirrer
2. temperaturereflux condenser
3. temperatureThe reaction mixture was heated
4. temperatureunder reflux for two days
5. customquenched with water (150 ml)
6. extractionextracted with ether (3×100 ml)
7. washThe organic layers combined were then washed with saturated NH4Cl (150 ml) and brine (150 ml)
8. dry with materialdried (MgSO4)
9. customthe solvent was removed under reduced pressure

ORD record

ord-76feb3e46be14cfc942253ac3c44acf4

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06506799B1