Triethylamine → Ethyl 3,4-dihydronaphthalene-2-carboxylate

Temperature

0 °C

A mixture of 2-ethoxycarbonyl-1,2,3,4-tetrahydro-1-naphthol (2.45 g, 11.1 mmol), triethylamine (2.70 g, 26.7 mmol) and tetrahydrofuran (50 ml) was cooled to 0° C., followed by adding dropwise thereto methanesulfonyl chloride (1.53 g, 13.3 mmol). The reaction mixture was stirred at 0-5° C. for 1.5 hours and then at room temperature for 7 hours, and allowed to stand overnight at room temperature. The reaction mixture was poured into a cold aqueous ammonium chloride solution and extracted twice with ethyl acetate, and the extract solution was washed with a saturated aqueous sodium hydrogencarbonate solution and a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:99) to obtain 2.12 g of ethyl 3,4-dihydronaphthalene-2-carboxylate.

1. additionby adding dropwise
2. waitat room temperature for 7 hours
3. waitto stand overnight at room temperature
4. extractionextracted twice with ethyl acetate
5. washthe extract solution was washed with a saturated aqueous sodium hydrogencarbonate solution
6. dry with materiala 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
7. distillationThe solvent was distilled off under reduced pressure
8. customthe resulting residue was purified by a silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:99)

ORD record

ord-1d39027ece104b95b15ea9d091039086

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06369110B1