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CID 406 → tert-Butyl[2,2-Dimethyl-5-(4-octanoylstyryl)-1,3-dioxan-5-yl]carbamate

HRID 1028883
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1028883
P(=O)([O-])[O-].[C:5]([O:9][C:10](=[O:22])[NH:11][C:12]1([CH:20]=O)[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14][CH2:13]1)([CH3:8])([CH3:7])[CH3:6].[C:23]([O-:26])([O-])=O.[K+].[K+].[CH2:29]1[CH2:33]O[CH2:31][CH2:30]1>CN(C=O)C>[C:5]([O:9][C:10](=[O:22])[NH:11][C:12]1([CH:20]=[CH:31][C:30]2[CH:7]=[CH:5][C:6]([C:23](=[O:26])[CH2:33][CH2:29][CH2:30][CH2:31][CH2:13][CH2:12][CH3:17])=[CH:33][CH:29]=2)[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14][CH2:13]1)([CH3:8])([CH3:7])[CH3:6]
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Komponenten

6

Edukt 4

HCID 406CID 406HCID 8028Tetrahydrofuran2×HCID 11430Potassium CarbonateHCID 24754730Tert-butyl (5-formyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamate

Produkt 1

HCID 123791953tert-Butyl[2,2-Dimethyl-5-(4-octanoylstyryl)-1,3-dioxan-5-yl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
72.5 °C

Versuchsvorschrift

A mixture of the Wittig reagent (23, X═O) or the phosphonate (0.3 mmol), aldehyde (24) (0.33 mmol), and K2CO3 (0.9 mmol) in a mixture of THF (3 ml) and DMF (1 ml) was heated at 70-75° C. under TLC and HPLC monitoring. After completion of the reaction, THF was evaporated and the reaction mixture was quenched with water and then extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated. After purification, the title compound (26) was recovered as white solid with 72% yield, mp 82-83° C.

Aufarbeitung

  1. customwas evaporated
  2. customthe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customAfter purification
  9. customthe title compound (26) was recovered as white solid with 72% yield, mp 82-83° C.

Quellen und Nachweise

ORD-Eintrag
ord-51e2f1efc7c34241b66e8e50c59a693e
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08735627B2

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