Sulfuric Acid → HCID 67099607, compound

A mixture of diethyl malonate (5.3 g, 33 mmol) and magnesium (0.80 g, 33 mmol) was treated with anhydrous EtOH 10 mL and 0.1 mL CCl4. The mixture was stirred at room temperature for 20 minutes and was then diluted with 50 mL anhydrous ether and refluxed for 1 hour under nitrogen. 1-(4-Chlorophenyl)cyclopentanecarbonyl chloride (7.3 g, 30 mmol) in 20 mL ether was then added dropwise to the above refluxed mixture, and the resulting mixture was refluxed for 20 minutes, M+1=341. The mixture was cooled to room temperature, diluted with 100 mL ether, washed with H2O (2×50 mL) and brine (20 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to give 11 g of the crude product as a pale yellow solid. The crude product was treated with concentrated H2SO4 (48 mL, 900 mmol) and stirred for 4 hours, M+1=321. The mixture was poured into 500 g ice and extracted with ether (3×100 mL). The organic layers were combined and washed with H2O (20 mL) and brine (20 mL), dried over anhydrous Na2SO4, concentrated in vacuo, and purified by column chromatography eluting with 10-20% ether/hexane to give the title compound (6.5 g) as a pale yellow solid. MS (m/z)=321 (M+H)+.

1. temperaturerefluxed for 1 hour under nitrogen
2. temperaturethe resulting mixture was refluxed for 20 minutes
3. temperatureThe mixture was cooled to room temperature
4. washwashed with H2O (2×50 mL) and brine (20 mL)
5. dry with materialdried over anhydrous Na2SO4
6. concentrationconcentrated in vacuo
7. customto give 11 g of the crude product as a pale yellow solid
8. stirringstirred for 4 hours
9. extractionextracted with ether (3×100 mL)
10. washwashed with H2O (20 mL) and brine (20 mL)
11. dry with materialdried over anhydrous Na2SO4
12. concentrationconcentrated in vacuo
13. custompurified by column chromatography
14. washeluting with 10-20% ether/hexane

ORD record

ord-3a6a27fac19340a1a18a7f06fb7595db

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07928139B2