Bromide ion → 5-(Cyclopent-1-enyl)-2-methylpentan-2-ol

5-(Cyclopent-1-enyl)-2-pentanone (5.95 g; 39 mmol) in ethyl ether (6 ml) was added dropwise to a 3M solution of methylnagnesium bromide in the same solvent (17 ml; 51 mmol) during 15 minutes. After 2 hours at reflux, the mixture was cooled down to room temperature, poured into ice (20 g), acidified with 5N HCl (20 ml) and extracted with MTBE (60 ml). The aqueous phase was separated and extracted again with MTBE (2×100 ml). The combined organic phases were washed with saturated NaHCO3 (80 ml), H2O (80 ml), brine (80 ml), dried over MgSO4 and concentrated in vacuo. Bulb-to-bulb distillation (80° C./0.06 torr) yielded quantitatively 5.84 g of 5-(cyclopent-1-enyl)-2-methylpentan-2-ol containing 11% of 5-cyclopentylidene-2-methylpentan-2-ol.

1. temperatureAfter 2 hours at reflux
2. extractionextracted with MTBE (60 ml)
3. customThe aqueous phase was separated
4. extractionextracted again with MTBE (2×100 ml)
5. washThe combined organic phases were washed with saturated NaHCO3 (80 ml), H2O (80 ml), brine (80 ml)
6. dry with materialdried over MgSO4
7. concentrationconcentrated in vacuo
8. distillationdistillation (80° C./0.06 torr)

ORD record

ord-13540fe1e8c841bc8238ffba1ff52f14

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06410000B1