Water → 3,3-Bis(ethoxycarbonyl)bicyclo[3.2.0]heptane

In a 250 ml round-bottomed flask equipped with mechanical stirring, reflux condenser, addition funnel and argon inlet was placed 20.2 g of XXI, 12.4 ml diethylmalonate, and 72 ml of dry t-butanol. The reaction mixture was refluxed and a solution of 19.9 g of potassium-t-butoxide in 123 ml of t-butanol was added over 6 hours. The reaction mixture was refluxed for 15 hours. The resulting reaction mixture was cooled by external application of an ice-water bath and an equal volume of water added. The mixture was extracted with ether. The ether extracts were washed with 3 N hydrochloric acid and 5% aqueous sodium bicarbonate, then dried (MgSO4), filtered and distilled in vacuo to yield 10.3 g of the compound XXII as a clear oil: bp 100°-105° C. (vacuum pump); ir (CHCl3) 5.85μ; nmr δ 1.22 (pair of t, J=7.OHz, broad), 4.37 (quartet, 4).

1. customIn a 250 ml round-bottomed flask equipped with mechanical stirring
2. temperaturereflux
3. additioncondenser, addition funnel and argon inlet
4. temperatureThe reaction mixture was refluxed
5. temperatureThe reaction mixture was refluxed for 15 hours
6. customThe resulting reaction mixture
7. temperaturewas cooled by external application of an ice-water bath
8. extractionThe mixture was extracted with ether
9. washThe ether extracts were washed with 3 N hydrochloric acid and 5% aqueous sodium bicarbonate
10. dry with materialdried (MgSO4)
11. filtrationfiltered
12. distillationdistilled in vacuo

ORD record

ord-60e5bf2467c548f6a57857da1b1df180

Source dataset

uspto-grants-1980_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04206127