Sodium Carbonate → (3R)-3-(triethylsilyloxy)-4-methyl-5-(2-methylthiazol-4-yl)-pent-4-enal

HRID 348247Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 348247
[CH2:1]([Si:3]([CH2:20][CH3:21])([CH2:18][CH3:19])[O:4][C@@H:5]([C:9]([CH3:17])=[CH:10][C:11]1[N:12]=[C:13]([CH3:16])[S:14][CH:15]=1)[CH2:6][CH:7]=C)[CH3:2].C[N+]1([O-])CC[O:26]CC1.[O-]S([O-])=O.[Na+].[Na+].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4].C([O-])([O-])=O.[Na+].[Na+]>C(O)(C)(C)C.C1C=CC=CC=1.[Os](=O)(=O)(=O)=O.O>[CH2:1]([Si:3]([CH2:20][CH3:21])([CH2:18][CH3:19])[O:4][C@@H:5]([C:9]([CH3:17])=[CH:10][C:11]1[N:12]=[C:13]([CH3:16])[S:14][CH:15]=1)[CH2:6][CH:7]=[O:26])[CH3:2]

Komponenten

10

Edukt 5

HCID 10340Sodium CarbonateHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 69507819(4R)-4-(triethylsilyloxy)-5-methyl-6-(2-methylthiazol-4-yl)-1,5-hexadieneHCID 178418268HCID 178418268, Verbindung

Produkt 1

HCID 86586609(3R)-3-(triethylsilyloxy)-4-methyl-5-(2-methylthiazol-4-yl)-pent-4-enal

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 30318Osmium TetroxideKatalysatorHCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittel2×HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

Osmium tetraoxide (1 wt % in THF, 20.3 mL) is added to a mixture of (4R)-4-(triethylsilyloxy)-5-methyl-6-(2-methylthiazol-4-yl)-1,5-hexadiene (13.5 g), H2O (21 mL), and N-methylmorpholine N-oxide (50% in THF, 10 mL, 0.048 mol) in tert-butanol (155 mL) at 0° C. After the resulting mixture is stirred for 12 hours, Na2SO3 (10 g) and water (5 mL) are added. The resulting solution is stirred at 25° C. for 30 minutes and then extracted with ether. The combined extracts are washed with brine, dried (Na2SO4), filtered, and concentrated. Purification by flash chromatography on SiO2 provides a 1:1 diastereomeric mixture of the diol as a colorless, viscous oil. Lead tetraacetate (19.1 g) is added portionwise over 5 minutes to a suspension of the diol (18.0 g) and Na2CO3 (8.67 g) in 500 mL of benzene at 0° C. After stirring for 15 minutes, the mixture is filtered through a SiO2 pad to afford the aldehyde product. The product is directly subjected to the next reaction.

Aufarbeitung

  1. stirringThe resulting solution is stirred at 25° C. for 30 minutes
  2. extractionextracted with ether
  3. washThe combined extracts are washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography on SiO2
  8. customprovides
  9. stirringAfter stirring for 15 minutes
  10. filtrationthe mixture is filtered through a SiO2 pad

Quellen und Nachweise

ORD-Eintrag
ord-0b0ad460ee4c4e698f70e2b0c81a848f
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176235B2

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