Tetramethylammonium hydroxide → 2-Fluoro-3-(methacryloyloxy)pentanoic acid

Under a nitrogen atmosphere, 5.81 g (25 mmol) of the ethyl 2-fluoro-3-(methacryloyloxy)pentanoate, and 250 mL of THF were cooled in a 1 L reaction vessel on an ice bath to an ice temperature, and thereto was added 250 g of a 2.38% by mass aqueous tetramethylammoniumhydroxide solution. The temperature of the mixture was elevated to the room temperature, followed by stirring the mixture at a room temperature for 5 hrs. After disappearance of the raw material was confirmed by thin layer chromatography, the solvent of the reaction liquid was distilled off under a reduced pressure. Water was added to the reaction mixture thus obtained, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with water twice, and the solvent was distilled off under a reduced pressure to obtain 4.59 g of 2-fluoro-3-(methacryloyloxy)pentanoic acid represented by the following formula (yield: 90%).

1. customwas elevated to the room temperature
2. customthe solvent of the reaction liquid
3. distillationwas distilled off under a reduced pressure
4. additionWater was added to the reaction mixture
5. customthus obtained
6. extractionthe mixture was extracted three times with ethyl acetate
7. washThe organic layer was washed with water twice
8. distillationthe solvent was distilled off under a reduced pressure

ORD record

ord-cac99016aabc4ccfa4e73e5bf9e8726c

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040221B2