Diethyl Ether → HCID 20158428, compound

A solution of 246 mg (1 mmole) of 3-chloro-4-t-butyldimethylsilylolxy-2-cyclopentenone in 5 ml of ether was added at -78° C. to a solution of 4-phenoxybutyllithium prepared from 1 equivalent of 4-phenoxybutyl bromide and 2 equivalents of t-butyllithium at -78° C. in 10 ml of ether. The mixture was stirred for 1.5 hours, and an aqueous solution of ammonium chloride was added. The reaction mixture was extracted with ether, dried over anhydrous magnesium sulfate, and concentrated. The resulting oily product was dissolved in 10 ml of tetrahydrofuran, and 2.4 ml of a 1 M tetrahydrofuran solution of tetrabutyl ammonium fluoride was added. The mixture was stirred for 10 hours. A saturated aqueous solution of sodium chloride was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated. The concentrate was chromatographed on a silica gel column to give 237 mg (84%) of 2-chloro-4-(4-phenoxybutyl)cyclopent-2-ene-1,4-diol.

1. extractionThe reaction mixture was extracted with ether
2. dry with materialdried over anhydrous magnesium sulfate
3. concentrationconcentrated
4. dissolutionThe resulting oily product was dissolved in 10 ml of tetrahydrofuran
5. addition2.4 ml of a 1 M tetrahydrofuran solution of tetrabutyl ammonium fluoride was added
6. stirringThe mixture was stirred for 10 hours
7. additionA saturated aqueous solution of sodium chloride was added to the reaction mixture
8. extractionthe mixture was extracted with ethyl acetate
9. dry with materialThe extract was dried over anhydrous sodium sulfate
10. concentrationconcentrated
11. customThe concentrate was chromatographed on a silica gel column

ORD record

ord-628944c646e94ddf85e9714ca61e6fed

Source dataset

uspto-grants-1987_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04711895