Ethyl Acetate → (25R)-16-oxo-26-hydroxycholesterol

HRID 327773

Reaktionsgleichung

Reaktionsgleichung von HRID 327773
[OH:1][C@H:2]1[CH2:27][C@@H:26]2[C@:13]([CH3:30])([CH2:14][CH2:15][C@H:16]3[C@H:25]2[CH2:24][CH:23]=[C:22]2[C@:17]3([CH3:29])[CH2:18][CH2:19][C@H:20]([OH:28])[CH2:21]2)[C@H:3]1[C@H:4]([CH3:12])[CH2:5][CH2:6][CH2:7][C@@H:8]([CH3:11])[CH2:9][OH:10].C([O-])(=O)C.[Na+].C(OCC)(=O)C>O.C(O)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[O:1]=[C:2]1[CH2:27][C@@H:26]2[C@:13]([CH3:30])([CH2:14][CH2:15][C@H:16]3[C@H:25]2[CH2:24][CH:23]=[C:22]2[C@:17]3([CH3:29])[CH2:18][CH2:19][C@H:20]([OH:28])[CH2:21]2)[C@H:3]1[C@H:4]([CH3:12])[CH2:5][CH2:6][CH2:7][C@@H:8]([CH3:11])[CH2:9][OH:10]

Komponenten

7

Edukt 3

HCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 11729441(3S,8S,9S,10R,13S,14S,16S,17R)-17-[(1R,5R)-6-hydroxy-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol

Produkt 1

HCID 13873472(25R)-16-oxo-26-hydroxycholesterolAusbeute 62,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 10219390chromium (VI) trioxideKatalysatorHCID 176Acetic AcidLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of chromium trioxide (80 mg) in water (0.4 ml) and acetic acid (0.8 ml) is added dropwise to a solution of (25R)-16β,26-dihydroxycholesterol (2) (0.500 g), and sodium acetate (2.48 g) in glacial acetic acid (90 ml), and is stirred for 18 hours at room temperature. The excess reagent is then destroyed with methanol (15 ml), and solvent is evaporated under reduced pressure. The resulting residue is diluted with water, and extracted with methylene chloride. The organic layer is washed with 5% K2CO3 and water, dried over sodium sulfate, and evaporated under reduced pressure to yield 0.48 g of crude product. The mixture is resolved by silica flash column chromatography (hexanes:ethyl acetate) to afford 0.313 g of (25R)-16-oxo-26-hydroxycholesterol (9). M.pt. 167°-169° C.

Aufarbeitung

  1. customThe excess reagent is then destroyed with methanol (15 ml), and solvent
  2. customis evaporated under reduced pressure
  3. additionThe resulting residue is diluted with water
  4. extractionextracted with methylene chloride
  5. washThe organic layer is washed with 5% K2CO3 and water
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customto yield 0.48 g of crude product

Quellen und Nachweise

ORD-Eintrag
ord-d41089aefb8840d7900b79b66001bbf6
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05274088

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