Water → HCID 19967160, compound

1.7 g of carbon tetrabromide and 1.15 g of triphenylphosphine were added to 10 ml of a solution of 0.70 g of ethyl 4-(3-hydroxy-1-propynyl)benzoate in methylene chloride at room temperature. The obtained mixture was stirred at that temperature for 13 hours, followed by the addition thereto of 20 ml of water. The obtained mixture was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified by silica gel chromatography (developer: 5% diethyl ether/n-hexane) to give 1.0 g of the title compound as a pale-yellow oil. 1H-NMR (400 MHz, CDCl3) δ(ppm); 1.38(t, J=7.2 Hz, 3H), 4.17(s, 2H), 4.36(q, J=7.2 Hz, 2H), 7.50(d, J=8.4 Hz, 2H), 7.99(d, J=8.4 Hz, 2H)

1. additionfollowed by the addition
2. extractionThe obtained mixture was extracted with ethyl acetate
3. washThe organic phase was washed with a saturated aqueous solution of common salt
4. dry with materialdried over anhydrous magnesium sulfate
5. distillationdistilled
6. customto remove the solvent
7. customThe residue was purified by silica gel chromatography (developer: 5% diethyl ether/n-hexane)

ORD record

ord-a1f3c7c1d870400096cd90761ecd659d

Source dataset

uspto-grants-1997_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05612356