2-Naphthalenecarboxaldehyde → HCID 13105363, Verbindung

HRID 365132

Reaktionsgleichung

Reaktionsgleichung von HRID 365132
[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])C=CC=CC=1.[CH:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][C:30]=1[CH:39]=O.CC(C)([O-])C.[K+]>CS(C)=O>[CH:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][C:30]=1/[CH:39]=[CH:10]\[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Komponenten

5

Edukt 3

HCID 62012-NaphthalenecarboxaldehydeHCID 2779280(5-Carboxypentyl)triphenylphosphanium bromideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 13105363HCID 13105363, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Triphenyl (5-carboxypentyl)phosphonium bromide (937 mg, 2.1 mmole) and 2-napthaldehyde (300 mg, 1.92 mmole) were dissolved in DMSO (50 mL, freshly distilled from CaH2) and potassium t-butoxide (540 mg, 4.8 mmole) was added. After stirring for 30 minutes the reaction was quenched with saturated NH4Cl solution (25 mL) and poured into ether. The ether layer was dried with saturated NaCl and MgSO4 and the solvent was evaporated. The resulting 1:1 mixture E/Z isomers were separated with flash chromatography eluting with ether/hexane/formic acid (10:89:1).

Aufarbeitung

  1. additionwas added
  2. customwas quenched with saturated NH4Cl solution (25 mL)
  3. additionpoured into ether
  4. dry with materialThe ether layer was dried with saturated NaCl and MgSO4
  5. customthe solvent was evaporated
  6. customThe resulting 1:1 mixture E/Z isomers were separated with flash chromatography
  7. washeluting with ether/hexane/formic acid (10:89:1)

Quellen und Nachweise

ORD-Eintrag
ord-3ad2552c093947eba337459f5871f91e
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04608390

Verknüpfte Notizen

Wird geladen…