Water → 8-Methylidene-1,4-dioxaspiro[4.5]decane

In a reactor under nitrogen atmosphere, 200 mL of THF was added to 41.2 g of methyltriphenylphosphonium bromide, and the mixture was cooled to −20° C., to which 12.9 g of t-BuOK was added, followed by stirring for 1 hour. A solution containing 15.0 g of 1.4-dioxaspiro[4.5]decan-8-one dissolved in 200 mL of THF was added dropwise thereto, followed by stirring at −20° C. for 1 hour. The temperature of the reaction mixture was increased to room temperature, and 200 mL of water was added to the reaction mixture, followed by extracting three times with 300 mL of toluene. The resulting organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was concentrated to about 200 mL under reduced pressure, and the concentrated solution was placed in 1,000 mL of hexane, followed by removing deposited solid matters. The solvent was distilled off from the resulting solution under reduced pressure, and the residue was purified by silica gel column chromatography to provide 10.6 g of 8-methylene-1,4-dioxaspiro[4.5]decane.

1. additionwas added
2. additionwas added dropwise
3. stirringby stirring at −20° C. for 1 hour
4. extractionby extracting three times with 300 mL of toluene
5. washThe resulting organic layer was washed with water
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationthe solvent was concentrated to about 200 mL under reduced pressure
8. customby removing
9. distillationThe solvent was distilled off from the resulting solution under reduced pressure
10. customthe residue was purified by silica gel column chromatography

ORD record

ord-588d163e99484988b391d3bf9fd2c8f6

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07914862B2