Cyclobutanone → Methyl cyclobutylideneacetate

Sodium hydride (>65% oil, 3.62 g, 95 mmol) was added to a tetrahydrofuran solution (200 mL) of trimethyl phosphonoacetate (18.21 g, 100 mmol) under ice cooling, and the mixture was stirred for 1 hour. To the reaction solution, a tetrahydrofuran solution (50 mL) of cyclobutanone (5.00 g, 71.4 mmol) was added dropwise, and the mixture was then brought to room temperature and stirred for 1.5 hours. To the reaction solution, a saturated aqueous solution of ammonium chloride was added, followed by extraction with hexane. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the compound of interest as a pale yellow oil substance (18.94 g, <100%).

1. customwas then brought to room temperature
2. stirringstirred for 1.5 hours
3. extractionfollowed by extraction with hexane
4. washThe organic layer was washed with saturated saline
5. dry with materialdried over anhydrous magnesium sulfate
6. distillationThe solvent was distilled off under reduced pressure
7. customto obtain the compound of interest as a pale yellow oil substance (18.94 g, <100%)

ORD record

ord-ceeb4bec7a1947ffad7a65b1f2f31929

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947738B2