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CID 406 → Methyl 6-dimethylamino-4,4-diphenyl-2-heptenoate

HRID 1461146
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1461146
P(=O)([O-])[O-].C[C:6](P(OC)(O)=O)([C:8]([O-:10])=[O:9])[CH3:7].[H-].[Na+].[CH3:18][N:19]([CH3:38])[CH:20]([CH3:37])[CH2:21][C:22]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)C=O.[CH3:39]CCC>O>[CH3:38][N:19]([CH3:18])[CH:20]([CH3:37])[CH2:21][C:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH:7]=[CH:6][C:8]([O:10][CH3:39])=[O:9]
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Komponenten

7

Edukt 5

HCID 406CID 406HCID 7843Butane3×HCID 24758Sodium hydrideHCID 37771754-Dimethylamino-2,2-diphenylpentanalHCID 53413272Trimethylphosphonoacetate

Produkt 1

HCID 53841050Methyl 6-dimethylamino-4,4-diphenyl-2-heptenoate

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 962WaterLösungsmittel

Versuchsvorschrift

The phosphonate anion was generated by dropwise addition of a solution of trimethylphosphonoacetate (182 mg) in 1,2-dimethylethane (DME, 1 ml) to a slurry of 80% sodium hydride (24 mg, prewashed with hexane) in DME (3 ml). After stirring at room temperature for 30 min, a solution of 4-dimethylamino-2,2-diphenylpentanal (281 mg), as prepared in Example 1, in DME (1 ml) was added slowly. The mixture was allowed to stir for 24 hours. Water was added, and the aqueous mixture was extracted with ethyl acetate (3×). The combined extracts were washed with water and brine (once each), and dried (MgSO4). Rotary evaporation of the solution gave a crude product which was flash-chromatographed over silica gel. Elution with chloroform/methanol (20:1) yielded 93 mg of methyl 6-dimethylamino-4,4-diphenyl-2-heptenoate.

Aufarbeitung

  1. additionwas added slowly
  2. stirringto stir for 24 hours
  3. extractionthe aqueous mixture was extracted with ethyl acetate (3×)
  4. washThe combined extracts were washed with water and brine (once each), and
  5. dry with materialdried (MgSO4)
  6. customRotary evaporation of the solution
  7. customgave a crude product which
  8. customwas flash-chromatographed over silica gel
  9. washElution with chloroform/methanol (20:1)

Quellen und Nachweise

ORD-Eintrag
ord-e8bbafcb2ffc4745ae6594eb8ac074df
Quelldatensatz
uspto-grants-1991_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05073629

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