Sodium borohydride → 2-Hydroxybicyclo[3.2.0]heptan-6-one

HRID 15185

Reaktionsgleichung

Reaktionsgleichung von HRID 15185
C([O:3][C:4]1(OCC)[CH2:10][CH:9]2[CH:5]1[CH2:6][CH2:7][C:8]2=[O:11])C.[BH4-].[Na+]>O1CCOCC1.OP([O-])(O)=O.[K+].Cl>[OH:11][CH:8]1[CH2:7][CH2:6][CH:5]2[CH:9]1[CH2:10][C:4]2=[O:3]

Komponenten

6

Edukt 2

HCID 4311764Sodium borohydrideHCID 125643656,6-Diethoxybicyclo[3.2.0]heptan-2-one

Produkt 1

HCID 134438072-Hydroxybicyclo[3.2.0]heptan-6-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittelHCID 516951Monobasic potassium phosphateLösungsmittel

Versuchsvorschrift

To a stirred solution of compound 1F in dioxane (50 mL) and 2M KH2PO4 (50 mL) was added NaBH4 (1.0 g, 26.4 mmol) over a 10 min-period, and the stirring was continued at RT for 1 hr. The reaction mixture was diluted with 2M HCl to adjust pH to 1, and stirred at RT for another 1 hr. The reaction was concentrated, dissolved in EtOAc, washed with water, dried over Na2SO4, and concentrated. Purification by silica gel chromatography (50% EtOAc in hexanes) provided the title compound (1.9 g) as a pale yellow oil.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in EtOAc
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (50% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-479eea0990784411930dc1e50887c603
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732480B2

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