Toluene → (+/-)-(1S,5R)-4-methylbicyclo[3.2.0]hept-3-en-6-one

3-Hydroxy-3-methylhept-6-enoic acid (5.24 g, 36.4 mmol) was dissolved in acetic anhydride (40 mL). To the solution, potassium acetate (12.52 g, 127 mmol) was added, and the mixture was stirred at room temperature for 2 hours. The reaction solution was heated to reflux and stirred for 4 hours. To the reaction solution, ice water and toluene were then added, and this mixture was stirred overnight at room temperature. The mixture was separated into aqueous and organic layers by the addition of diethyl ether and saturated saline. Then, the organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography to obtain the compound of interest as a pale yellow oil substance (1.10 g, 17%, diastereomeric mixture).

1. temperatureThe reaction solution was heated
2. temperatureto reflux
3. stirringstirred for 4 hours
4. stirringthis mixture was stirred overnight at room temperature
5. customThe mixture was separated into aqueous and organic layers
6. additionby the addition of diethyl ether and saturated saline
7. washThen, the organic layer was washed with saturated saline
8. dry with materialdried over anhydrous magnesium sulfate
9. distillationthe solvent was distilled off under reduced pressure
10. customThe residue was purified by silica gel chromatography
11. customto obtain the compound of interest as a pale yellow oil substance (1.10 g, 17%, diastereomeric mixture)

ORD record

ord-f741940b88244f6ab1ed72cf06d4f434

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947738B2