Dimethylformamide → Allyl 4-[(4-methoxybenzyl)oxy]-4-oxobutyl succinate

Temperature

100 °C

To a suspension of commercially available sodium 4-hydroxybutyrate (756 mg, 6.00 mmol) in N,N-dimethylformamide (10 ml) was added 4-methoxybenzyl chloride (987 mg, 6.30 mmol), and the mixture was heated at 100° C. for 3 hours. The reaction mixture was cooled, and allyl 4-chloro-4-oxobutyrate (1.06 g, 6.02 mmol) obtained from Example 14-(1), triethylamine (920 μl, 6.60 mmol), and 4-(N,N-dimethylamino)pyridine (10 mg) were added thereto at 0° C. The mixture was stirred at room temperature for 18 hours, and the obtained mixture was diluted with ethyl acetate, then the resulting solution was washed successively with water, a saturated aqueous solution of sodium hydrogen carbonate, a saturated aqueous solution of ammonium chloride, and an aqueous solution of sodium chloride. The solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to give an oily residue. The residue was subjected to chromatography on a silica gel (50 g) column (eluent; hexane:ethyl acetate=3:1˜2:1) to afford the title compound (1.52 g, 70% yield) as a colorless oil.

1. temperatureThe reaction mixture was cooled
2. customat 0° C
3. washthe resulting solution was washed successively with water
4. dry with materialThe solution was dried over anhydrous magnesium sulfate
5. distillationthe solvent was distilled off under reduced pressure
6. customto give an oily residue

ORD record

ord-6a6751f01a83454a82f29511a6fe7c60

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07230023B2