Water → 2-Chloro-4-octylcyclopent-2-ene-1,4-diol

Temperature

-78 °C

108 mg of 3-chloro-4-t-butyldimethylsilyloxy-2-cyclopentenone was dissolved in 4 ml of ether, and the solution was cooled to -78° C. Then, 0.79 ml of a 0.72 M tetrahydrofuran solution of octyl magnesium bromide was added. The mixture was stirred for 10 minutes, and water was added. The mixture was extracted with ether, and the extract was dried over anhydrous magnesium sulfate, filtered, and concentrated. The resulting oily product was dissolved in 6 ml of tetrahydrofuran, and 1.1 ml of a 1 M tetrahydrofuran solution of tetrabutyl ammonium fluoride was added. The mixture was stirred for 2 days. A saturated aqueous solution of sodium chloride was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, filtered, and concentrated. The concentrate was chromatographed on a silica gel column to give 92 mg (yield 83%) of 2-chloro-4-octylcyclopent-2-ene-1,4-diol.

1. extractionThe mixture was extracted with ether
2. dry with materialthe extract was dried over anhydrous magnesium sulfate
3. filtrationfiltered
4. concentrationconcentrated
5. dissolutionThe resulting oily product was dissolved in 6 ml of tetrahydrofuran
6. addition1.1 ml of a 1 M tetrahydrofuran solution of tetrabutyl ammonium fluoride was added
7. stirringThe mixture was stirred for 2 days
8. additionA saturated aqueous solution of sodium chloride was added
9. extractionthe mixture was extracted with ethyl acetate
10. dry with materialThe extract was dried over anhydrous sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated
13. customThe concentrate was chromatographed on a silica gel column

ORD record

ord-96c18c923db946b1804b32b07089eb58

Source dataset

uspto-grants-1987_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04711895