Water → HCID 57827205, compound

7,7-Dimethoxyhept-1-en-4-ol obtained in Preparation Example 59-(1) (6.16 g) was dissolved in 1-methyl-2-pyrrolidinone (60 mL), and the solution was cooled in an ice bath under a nitrogen atmosphere. Then, sodium hydride (60%, 2.12 g) was added, followed by stirring for 10 minutes. Methyl iodide (6.61 g, 2.28 g/cm3) was further added and the mixture was further stirred for two hours and 10 minutes. After slowly adding water, ethyl acetate was added, followed by further stirring. The aqueous layer was separated and then the organic layer was sequentially washed with a saturated ammonium chloride solution, water and brine. The resulting organic layer was dried over anhydrous magnesium sulfate, and the solid was removed by filtration. The filtrate was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain the title compound (5.83 g).

1. temperaturethe solution was cooled in an ice bath under a nitrogen atmosphere
2. stirringthe mixture was further stirred for two hours and 10 minutes
3. customThe aqueous layer was separated
4. washthe organic layer was sequentially washed with a saturated ammonium chloride solution, water and brine
5. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
6. customthe solid was removed by filtration
7. concentrationThe filtrate was concentrated under reduced pressure
8. custompurified by silica gel column chromatography

ORD record

ord-78495d90f41545ddb34886bc6e181d37

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158620B2