Methyl chloroformate → HCID 59395083, compound

Temperature

0 °C

4-Chloro-2-cyclopentylphenol (2.366 g, 7.94 mmol) was dissolved in dichloromethane (20 mL) and triethylamine (2.2 mL, 15.9 mmol). The solution was cooled to 0° C. and treated with methyl chloroformate (920 μL, 11.91 mmol) and allowed to warm to room temperature over 16 h. The reaction was quenched with 3 mL saturated NaHCO3, washed with 50% saturated NaHCO3 (1×50 mL) and brine (1×50 mL), then dried over Na2SO4. Filtration, followed by concentration in vacuo yielded an oil that was purified by silica gel chromatography (20% ethyl acetate/hexane) to yield 4-chloro-2-cyclopentylphenyl methyl carbonate as a colorless oil. 1H NMR (400.0 MHz, DMSO-d6) δ 7.31-7.28 (m, 1H), 7.20-7.13 (m, 1H), 7.06 (d, J=8.6 Hz, 1H), 3.93 (d, J=3.1 Hz, 3H), 3.18-3.09 (m, 1H), 2.08-2.01 (m, 2H), 1.87-1.78 (m, 2H), 1.75-1.65 (m, 2H), 1.61-1.51 (m, 2H).

1. temperatureto warm to room temperature over 16 h
2. customThe reaction was quenched with 3 mL saturated NaHCO3
3. washwashed with 50% saturated NaHCO3 (1×50 mL) and brine (1×50 mL)
4. dry with materialdried over Na2SO4
5. filtrationFiltration
6. concentrationfollowed by concentration in vacuo
7. customyielded an oil that
8. customwas purified by silica gel chromatography (20% ethyl acetate/hexane)

ORD record

ord-75a8edb0902d4d35bdce9d778bfd2cc5

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999976B2