Aluminium lithium hydride → 4-Fluoro-3-(hydroxymethyl)benzaldehyde

2.8 g of 5-Dimethoxymethyl-2-fluorobenzaldehyde was dissolved in 40 ml of diethyl ether, and 0.38 g of lithium aluminum hydride was added under ice-cooling. After being stirred at room temperature for 5 minutes, the reaction solution was ice-cooled and diethylether-water was added. When the insoluble precipitate adhered to the wall of the flask, the reaction solution was dried over anhydrous magnesium sulfate, then evaporated. The residue was dissolved in 25 ml of dichloromethane, and 8 ml of trifluoroacetic acid was added. The reaction mixture was stirred at room temperature for 2.5 hours, the reaction solution was diluted with water and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then evaporated. The residue was subjected to silica gel column chromatography (30% ethyl acetate-hexane), to give 1.6 g of the title compound.

1. temperaturecooling
2. temperaturecooled
3. dry with materialthe reaction solution was dried over anhydrous magnesium sulfate
4. customevaporated
5. dissolutionThe residue was dissolved in 25 ml of dichloromethane
6. addition8 ml of trifluoroacetic acid was added
7. stirringThe reaction mixture was stirred at room temperature for 2.5 hours
8. additionthe reaction solution was diluted with water
9. extractionthe mixture was extracted with ethyl acetate
10. washThe organic layer was washed with saturated brine
11. dry with materialdried over anhydrous magnesium sulfate
12. customevaporated

ORD record

ord-2c785f1a1cb34eabbda4cc426d6df20c

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07544835B2