Triethylamine → HCID 19591478, compound

1.30 g of dimethyl 4-hydroxymethylphthalate was dissolved in 15 ml of ethyl acetate, and 0.58 ml of methanesulfonyl chloride and 1.55 ml of triethylamine were added under cooling with ice with stirring, followed by stirring at room temperature overnight. Insoluble matters were filtered off, and then, the solvent was distilled off under reduced pressure. The residue was dissolved in 13 ml of dimethylformamide, and then, 0.54 g of sodium cyanide was added, followed by stirring at room temperature for 3 hours. The reaction solution was extracted by an addition of ethyl ether and water, and the organic layer was post-treated in accordance with a usual method. Then, the product was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to obtain 0.78 g of the above identified compound as a colorless oily substance.

1. temperatureunder cooling with ice
2. stirringby stirring at room temperature overnight
3. filtrationInsoluble matters were filtered off
4. distillationthe solvent was distilled off under reduced pressure
5. dissolutionThe residue was dissolved in 13 ml of dimethylformamide
6. addition0.54 g of sodium cyanide was added
7. stirringby stirring at room temperature for 3 hours
8. extractionThe reaction solution was extracted by an addition of ethyl ether and water
9. additionthe organic layer was post-treated in accordance with a usual method
10. customThen, the product was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)
11. customto obtain 0.78 g of the

ORD record

ord-7643ca17232348899c526ac3adc62518

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06011174