Triethylamine → HCID 57701306, compound

Temperature

2.5 °C

2-Phenoxyethanol (50 g, 0.362 mol) was dissolved in dichloromethane (500 ml) and the solution was cooled to 0-5° C. Triethylamine (101 ml, 0.724 mol) was added to the cooled solution followed by pivaloyl chloride (53.5 ml, 0.434 mol) maintaining the temperature, below 5° C. After additions the mixture was stirred at 5° C. for 30 min and at room temperature for 12 h. The reaction was quenched by addition of 1M HCl-solution (300 ml) and stirred vigorously. The phases were separated and organic phase was washed with saturated NaHCO3-solution (2×150 ml), water (1×100 ml) and brine (1×100 ml). After drying (Na2SO4) and filtration the solvent was evaporated yielding the title compound (76.78 g, 0.345 mol, 95%) as a yellow oil. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 7.31-7.27 (2H, m, ArH), 6.96-6.93 (3H, m, ArH), 4.34 (2H, m, CH2CH2OPiv), 4.19 (2H, m, ArOCH2CH2), 1.13 (9H, s, 3×Me). 13C-NMR (100 MHz, DMSO-d6) δ (ppm): 177.7, 158.7, 130.1, 121.1, 114.9, 66.1, 62.9, 38.5, 27.6.

1. temperaturemaintaining the temperature, below 5° C
2. customThe reaction was quenched by addition of 1M HCl-solution (300 ml)
3. stirringstirred vigorously
4. customThe phases were separated
5. washorganic phase was washed with saturated NaHCO3-solution (2×150 ml), water (1×100 ml) and brine (1×100 ml)
6. customAfter drying
7. filtration(Na2SO4) and filtration the solvent
8. customwas evaporated

ORD record

ord-f5330ad4be3f489a8ac6e3cceeed5e50

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09321712B2