Tetrahydrofuran → 1-Methoxy-3,3-dimethylhexa-1,5-diene

Temperature

0 °C

To a freshly prepared tetrahydrofuran (300 mL) solution of lithium diisopropylamide (0.19 mol) under nitrogen at 0° C. was added dropwise in 30 minutes a tetrahydrofuran (200 mL) solution of diphenyl(methoxymethyl)phosphinoxide (49.5 g, 0.2 mol). After stirring for 15 minutes at 0° C., a tetrahydrofuran (100 mL) solution of 2,2-dimethylpent-4-enal (24.5 g, 0.22 mol) was added dropwise in 20 minutes to the cherry-colored mixture. After 15 minutes, the mixture was warmed to room temperature and then refluxed for 5 hours. The mixture was cooled to room temperature, charged with water (20 mL), and cooled at 0° C. under vigorous stirring. The resulting solid was filtered, washed with hexanes, and discarded. The filtrates were collected and distilled at 101-102° C. (155 mmHg) to give the title compound as a colorless oil.

1. waitAfter 15 minutes
2. temperaturethe mixture was warmed to room temperature
3. temperaturerefluxed for 5 hours
4. temperatureThe mixture was cooled to room temperature
5. temperaturecooled at 0° C. under vigorous stirring
6. filtrationThe resulting solid was filtered
7. washwashed with hexanes
8. customThe filtrates were collected
9. distillationdistilled at 101-102° C. (155 mmHg)

ORD record

ord-2cfa739e7ec74b7db335b539e77ae1e5

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07880014B2