Sulfuric Acid → HCID 13924084, compound

Temperature

-30 °C

All work is performed in an inert atmosphere using anhydrous tetrahydrofuran. The starting material, 3-(5-cyclopenten-3-yl) valeraldehyde {2-cyclopentene-1-pentanal} (75 g, 0.493 moles) is dissolved in tetrahydrofuran (750 ml) and cooled in a -30° C. ethanol/dry ice bath. Ethyl magnesium bromide (0.493 moles) is added dropwise to the stirring reaction mixture for a period of over 2 hours. The reaction is warmed to 0° C. and water (100 ml), followed by 15% sulfuric acid (200 ml), is added. The aqueous layer is extracted with ether (2×300 ml) and the organic extracts are combined, reduced in volume and washed with brine (400 ml). The product is dried over anhydrous sodium sulfate and the remaining solvent removed under vacuum leaving a clear yellow oil. The crude product is chromatographed on silica gel and subsequently kugelrohred under vacuum leaving clear, colorless oil (10.2 g, 0.056 moles).

1. temperatureThe reaction is warmed to 0° C.
2. additionis added
3. extractionThe aqueous layer is extracted with ether (2×300 ml)
4. washwashed with brine (400 ml)
5. dry with materialThe product is dried over anhydrous sodium sulfate
6. customthe remaining solvent removed under vacuum
7. customleaving a clear yellow oil
8. customThe crude product is chromatographed on silica gel
9. customleaving clear

ORD record

ord-a798ca8805c3407eb1901260aed8dce8

Source dataset

uspto-grants-1987_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04689345