Methyl iodide → 7-Methyl-1,4-dioxaspiro[4.5]decan-8-one

Under a nitrogen atmosphere, to a solution of lithium bis(trimethylsilyl)amide (1M, 100 ml, 100 mmol) in tetrahydrofuran (200 ml) was added dropwise a solution of 1,4-dioxaspiro[4.5]decan-8-one (15.6 g, 100 mmol) in tetrahydrofuran (50 ml) at −78° C. over about 30 min, and the mixture was stirred for 30 min. Then, methyl iodide (2.5 ml, 120 mmol) was added dropwise over 5 min, and the mixture was stirred at −78° C. for 30 min, and at room temperature for 2 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted three times with diethyl ether. The combined organic layers were dried over magnesium sulfate. Magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography to give the title compound (10.6 g, yield 62%).

1. stirringthe mixture was stirred at −78° C. for 30 min
2. waitat room temperature for 2 hr
3. extractionthe mixture was extracted three times with diethyl ether
4. dry with materialThe combined organic layers were dried over magnesium sulfate
5. customMagnesium sulfate was removed by filtration
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe residue was purified by silica gel chromatography

ORD record

ord-d9e3628c2343459f9827cf54cd27a9cc

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299070B2