Tetrahydrofuran → 1-(2,2-Dimethoxyethyl)cyclopropan-1-ol

Temperatur

0 °C

To a 1.0 L RBF containing methyl 3,3-dimethoxypropanoate (17.6500 g, 119 mmol) was added THF (150 ml) and diethyl ether (150 ml), and the mixture was allowed to stir at 0° C. for 15 min. At this time, tetra-isopropoxy titanium (6.98 ml, 23.8 mmol) was added in one portion before the dropwise addition of ethylmagnesium bromide (99.3 ml, 298 mmol) via syringe. The reaction was allowed to warm to 23° C. and stir for 14 hours before being re-chilled to 0° C. After 5 min at this temp, water (15 ml) was added and a solid formed. Diethyl ether (200 ml) was added and the quenched reaction was stirred for 10 min before filtering through a plug of magnesium sulfate. The filtrate was dried with additional magnesium sulfate, filtered and concentrated to give a colorless oil. The crude material was used directly in the next reaction.

1. temperatureto warm to 23° C.
2. stirringstir for 14 hours
3. temperaturebefore being re-chilled to 0° C
4. customa solid formed
5. customthe quenched reaction
6. stirringwas stirred for 10 min
7. filtrationbefore filtering through a plug of magnesium sulfate
8. dry with materialThe filtrate was dried with additional magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customto give a colorless oil

ORD-Eintrag

ord-6fee97b78a4a47b3b51493577f890479

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07745484B2