Iodoethane → 3-Ethyltetrahydro-4H-pyran-4-one

Temperature

-78 °C

To a mixture of tetrahydropyran-4 one (5 g, 0.05 mol) and hexamethylphosphoramide (9 mL) in tetrahydrofuran (100 mL) was added lithium diisopropylamide (34.7 mL, 0.062 mol) dropwise at −78° C. under N2. After the addition the mixture was stirred for 0.5 h at −78° C. Iodoethane (7.78 g, 0.199 mol) was added to the mixture dropwise. The ddresulting mixture was stirred for 12 hours at room temperature. TLC (petroleum ether:ethyl acetate=4:1) indicated the reaction was not complete, the mixture was quenched with aqueous ammonium chloride (100 mL), extracted with ethyl acetate (3×50 mL), the combined organic layers was concentrated in vacuo and the residue was purified by chromatography on silica using petroleum ether: ethyl acetate from 15:1 to 10:1 to yield compound the title compound (2.5 g, 39.1%) as a colorless liquid. 1H NMR (400 MHz, CD3OD) δ (ppm): 4.15 (m, 2H), 3.80 (m, 1H), 3.45 (m, 1H), 2.58 (m, 1H), 2.48 (m, 2H), 1.81 (m, 1H), 1.30 (m, 1H), 0.92 (m, 3H).

1. additionAfter the addition the mixture
2. stirringThe ddresulting mixture was stirred for 12 hours at room temperature
3. customthe mixture was quenched with aqueous ammonium chloride (100 mL)
4. extractionextracted with ethyl acetate (3×50 mL)
5. concentrationthe combined organic layers was concentrated in vacuo
6. customthe residue was purified by chromatography on silica

ORD record

ord-a31e6656f00348889cd1a8effd265550

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906911B2