Diethyl Oxalate → HCID 67529552, compound

Temperature

-78 °C

LHMDS solution (39.3 mL, 39.3 mmol, 1M in hexanes) was added to 200 mL of diethyl ether and the mixture was cooled to −78° C. Cyclohexyl ethyl ketone (5.0 g, 35.7 mmol) dissolved in 50 mL of ether was added dropwise, and the resulting mixture was stirred at −78° C. for 1 h. Diethyl oxalate (5.6 mL, 41.1 mmol) was then added dropwise, and the cooling bath was removed and the mixture was allowed to come to room temperature. After the mixture was stirred for 16 h, 1M hydrochloric acid (200 mL) was added and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (3×100 mL) and the combined organic layers were dried over MgSO4 and concentrated. The crude oil was purified by chromatography (0-20% EtOAc/hexanes) to give 5.36 g of the title compound. MS: (−) m/z 239.33 (M−1).

1. additionwas added dropwise
2. customthe cooling bath was removed
3. customto come to room temperature
4. stirringAfter the mixture was stirred for 16 h
5. addition1M hydrochloric acid (200 mL) was added
6. customthe organic layer was separated
7. extractionThe aqueous layer was extracted with CH2Cl2 (3×100 mL)
8. dry with materialthe combined organic layers were dried over MgSO4
9. concentrationconcentrated
10. customThe crude oil was purified by chromatography (0-20% EtOAc/hexanes)

ORD record

ord-d782036cd55c402580ddebea6f1d6879

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08269008B2