Acetic Acid → 5-Hydroxy-hexahydro-pentalen-2-one

HRID 1660297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1660297
[BH4-].[Na+].[CH:3]12[CH2:10][C:9](=[O:11])[CH2:8][CH:7]1[CH2:6][C:5](=[O:12])[CH2:4]2.CC(C)=O.C(O)(=O)C>C(Cl)Cl.C(O)C.O>[OH:12][CH:5]1[CH2:4][CH:3]2[CH:7]([CH2:8][C:9](=[O:11])[CH2:10]2)[CH2:6]1

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 180AcetoneHCID 103526cis-Tetrahydropentalene-2,5(1H,3H)-dioneHCID 4311764Sodium borohydride

Produkt 1

HCID 130418335-Hydroxy-hexahydro-pentalen-2-oneAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

1.1 g of sodium borohydride (0.029 mol) is added with stirring to a solution of 11.6 g of bicyclo[3.3.0]octane-3,7-dione (8.4×10-2 mol) in 100 ml of methylene chloride and 100 ml of ethanol. After 45 minutes at this temperature, the excess reagent is decomposed by slowly adding 20 ml of acetone. The mixture is then neutralized with 1.4 ml of acetic acid, and evaporated under vacuum to afford a residue which is taken up in water and methylene chloride. The organic phase is evaporated to dryness and filtered on silica gel (70:30 hexane:ethyl ether as eluent) to afford 9.1 g of 7ξ-hydroxy-bicyclo[3.3.0]octan-3-one.

Aufarbeitung

  1. customevaporated under vacuum
  2. customto afford a residue which
  3. customThe organic phase is evaporated to dryness
  4. filtrationfiltered on silica gel (70:30 hexane:ethyl ether as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-a903e17f43fe4c0a97a3f61c7791fb6d
Quelldatensatz
uspto-grants-1981_12
Patentnummer
US04307112

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