Hydrogen Peroxide → Benzyl 5-hydroxy-2,2-dimethylpentanoate

HRID 1866613

Reaktionsgleichung

Reaktionsgleichung von HRID 1866613
[CH3:1][C:2]([CH3:16])([CH2:13][CH:14]=[CH2:15])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].B1C2CCCC1CCC2.C([O-])(=[O:28])C.[Na+].OO>C1COCC1>[OH:28][CH2:15][CH2:14][CH2:13][C:2]([CH3:16])([CH3:1])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4]

Komponenten

6

Edukt 4

HCID 784Hydrogen PeroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 517045Sodium AcetateHCID 66973286Benzyl 2,2-dimethylpent-4-enoate

Produkt 1

HCID 66972971Benzyl 5-hydroxy-2,2-dimethylpentanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of benzyl 2,2-dimethylpent-4-enoate (5.74 g, 26.3 mmol, prepared according to Step A) in THF (100 mL) was added a solution of 9-BBN (63.1 mL, 31.6 mmol, 0.5 M in THF) over 20 minutes, while under nitrogen. The reaction was allowed to stir at ambient temperature for 17 hours. An aqueous solution of sodium acetate (7.3 g, 89 mmol, in 18 mL of water) was then added, followed by the slow addition of aqueous hydrogen peroxide (18 mL, 30% by weight solution) with occasional chilling in a 0° C. bath. This mixture was allowed to stir at ambient temperature for 1.5 hours, before being extracted with ethyl acetate. The combined organics were washed with saturated brine. The organics were then dried over sodium sulfate, filtered, and concentrated in vacuo to give a residue that was purified by silica gel chromatography, eluting with a gradient of MeOH:DCM—1:99 to 10:90, to give the title compound. MS: m/z=237 (M+1).

Aufarbeitung

  1. temperaturewith occasional chilling in a 0° C. bath
  2. stirringto stir at ambient temperature for 1.5 hours
  3. extractionbefore being extracted with ethyl acetate
  4. washThe combined organics were washed with saturated brine
  5. dry with materialThe organics were then dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a residue that
  9. customwas purified by silica gel chromatography
  10. washeluting with a gradient of MeOH

Quellen und Nachweise

ORD-Eintrag
ord-6a8db5db14804a738b46f0f98418a88e
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629338B2

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