Sodium hydride → 3-(3,3-Diethoxypropoxy)-2-methylprop-1-ene

To a stirred solution of 3,3-diethoxy-1-propanol (3.0 g, 22.2 mmol) in anhydrous THF (50 mL) was added sodium hydride (60% dispersion in mineral oil, 1.07 g, 26.6 mmol). The reaction mixture was stirred for 30 minutes, and 3-bromo-2-methyl-1-propene (3.63 g, 24.5 mmol) then added. The reaction mixture was then stirred for a further 18 hours. The reaction mixture was quenched with saturated sodium hydrogen carbonate and extracted with ethyl acetate (×3). The combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution and brine, dried (sodium sulfate), filtered and concentrated under reduced pressure to afford an oil (2.25 g, 50%). The material used in the next step without further purification.

1. stirringThe reaction mixture was then stirred for a further 18 hours
2. customThe reaction mixture was quenched with saturated sodium hydrogen carbonate
3. extractionextracted with ethyl acetate (×3)
4. washThe combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution and brine
5. dry with materialdried (sodium sulfate)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure

ORD record

ord-f6fd28a8e9c648ed9a08fe5b3921417c

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012644B2