Water → HCID 16093516, compound

3.0 g (62.4 mmol) of 50% sodium hydride dispersion in mineral oil are placed in 50 ml of tetrahydrofuran and 40 ml of dimethylformamide, a solution of 10.0 g (62.4 mmol) of 3-hydroxy-2-methylenepropionaldehyde-diethylacetal in 10 ml of tetrahydrofuran is slowly added dropwise at 0°, and the mixture is stirred at 0° for 2 hours. The mixture is diluted with 15 ml of tetrahydrofuran and 10 ml of dimethylformamide and stirred at room temperature for a further 2 hours. 7.2 ml (62.4 mmol) of benzyl chloride in 10 ml of dimethylformamide are then added at 0°, and the mixture is stirred at room temperature for 18 hours. Water is added to the reaction mixture, which is then extracted three times with ethyl acetate, and the organic phases are washed with saturated sodium chloride solution. The organic phases are combined, dried over Na2SO4, filtered and concentrated by evaporation. The residue is chromatographed on silica gel with methylene chloride, yielding 3-benzyloxy-2-methylenepropionaldehyde-diethylacetal in the form of a pale yellowish liquid.

1. stirringstirred at room temperature for a further 2 hours
2. stirringthe mixture is stirred at room temperature for 18 hours
3. extractionis then extracted three times with ethyl acetate
4. washthe organic phases are washed with saturated sodium chloride solution
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated by evaporation
8. customThe residue is chromatographed on silica gel with methylene chloride

ORD record

ord-a096da25787f4b4b821e3da5946b1f23

Source dataset

uspto-grants-1994_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05294734