Water → HCID 57827343, compound

4,4-Dimethoxybutyraldehyde (Org. Biomol. Chem. 4 (2006) 2158) (5.47 g) was dissolved in THF (55 mL), and the solution was cooled in an ice bath under a nitrogen atmosphere. Then, a solution of allylmagnesium chloride in THF (62.1 mL, 1 M) was slowly added. After completion of the addition, the mixture was stirred for three hours. After slowly adding water, ethyl acetate and a saturated ammonium chloride solution were 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 (5.55 g).

1. temperaturethe solution was cooled in an ice bath under a nitrogen atmosphere
2. additionAfter completion of the addition
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-e6f41bb4ffff4710ba00b2d39ea47e03

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158620B2