Water → cis-4-Tetrahydropyranyloxy 2-cyclopentenol

Dissolve (-)-acetic acid cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl ester (106 mg, 0.47 mmol, prepared in example 11) in THF/methanol/water (1.5/0.5/0.5 mL). Add lithium hydroxide monohydrate (0.57 mmol) with stirring. After stirring for about 3 hours at room temperature, dilute the reaction with tert-butyl methyl ether (10 mL) and water (10 mL). Extract with tert-butyl methyl ether (2×10 mL). Combine the organic extracts, dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (silica gel, 2.5 g, 1.7×2.5 cm column, 50% ethyl acetate/hexane, 150 mL) to provide the title compound (80 mg, 93% yield), [α]20D =+9.9°, (c=0.98, chloroform).

1. additiondilute
2. extractionExtract with tert-butyl methyl ether (2×10 mL)
3. dry with materialCombine the organic extracts, dry over anhydrous magnesium sulfate
4. filtrationfilter
5. concentrationconcentrate under vacuum
6. customPurify the residue by flash chromatography (silica gel, 2.5 g, 1.7×2.5 cm column, 50% ethyl acetate/hexane, 150 mL)

ORD-Eintrag

ord-10b7633aee1e4fbb926d469c9902bde4

Quelldatensatz

uspto-grants-1998_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05808112