Imidazole → (1R,4S)-4-((tert-Butyldimethylsilyl)oxy)cyclopent-2-en-1-ol

To a solution of (1R,3S)-(+)-4-cyclopentene-1,3-diol 1-acetate (1.0 g, 7.03 mmol) (Aldrich) and imidazole (960 mg, 14.06 mmol) (Aldrich) in tetrahydrofuran (35 mL) was added tert-butyldimethylsilyl chloride (1.27 g, 8.44 mmol) (Aldrich). The mixture was allowed to warm slowly to room temperature, stirred overnight and then partitioned between ethyl acetate and water. The organic layer was collected, dried over sodium sulfate, filtered and concentrated to a residue that was dissolved in methanol (45 mL). To this solution was added potassium carbonate (1.17 g, 8.44 mmol) and the mixture stirred overnight. The next morning the reaction mixture was partitioned between ethyl acetate and water. The organic layer was collected, dried over sodium sulfate, filtered and concentrated to a residue that was purified by silica gel column chromatography with a 0–30% diethyl ether in hexanes gradient to give (−)-(1R,4S)-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enol as a colorless oil. (Yield 1.29 g, 85%).

1. custompartitioned between ethyl acetate and water
2. customThe organic layer was collected
3. dry with materialdried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated to a residue that
6. dissolutionwas dissolved in methanol (45 mL)
7. stirringthe mixture stirred overnight
8. customThe next morning the reaction mixture was partitioned between ethyl acetate and water
9. customThe organic layer was collected
10. dry with materialdried over sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated to a residue that
13. customwas purified by silica gel column chromatography with a 0–30% diethyl ether in hexanes gradient

ORD record

ord-6e8dc43323f84c3d91bfc5d3df233a6b

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07115740B2