Triphenylphosphine → HCID 22949959, Verbindung

HRID 1383894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383894
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH3:14][N:15]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:16][CH2:17]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH2:19]([N:15]([CH2:16][CH2:17][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1)[CH3:14])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 10657884Dodecyl(2-hydroxyethyl)methylamine

Produkt 1

HCID 22949959HCID 22949959, VerbindungAusbeute 887,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of methyl 3-(4-hydroxyphenyl)propionate (10.0 g, 55. 5 mmol), N-methyl-N-dodecylethanolamine (13.5 g, 55.5 mmol) and triphenylphosphine (16.0 g, 61.0 mmol) in dry tetrahydrofuran (200 ml) was treated at 22° C. with diisopropyl azodicarboxylate (12.3 g, 61.0 mmol) added dropwise over 50 min. After 3 h at 22° C., the reaction mixture was evaporated under reduced pressure and the residue was triturated with hexane. The solid formed was filtered, washed with hexane and the combined filtrate was chromatographed on silica gel using a gradient of ethyl acetate in hexane (20%-60%) as eluent. Distillation under vacuum then gave 18.0 g (75%) of 3-{4-[2-(N-dodecyl-N-methylamino)ethoxy]phenyl} propanoic acid, methyl ester as a clear oil: b.p. 180-183° C./0.02 torr (bulb to bulb distillation, air bath temperature).

Aufarbeitung

  1. additionadded dropwise over 50 min
  2. customthe reaction mixture was evaporated under reduced pressure
  3. customthe residue was triturated with hexane
  4. customThe solid formed
  5. filtrationwas filtered
  6. washwashed with hexane
  7. customthe combined filtrate was chromatographed on silica gel using a gradient of ethyl acetate in hexane (20%-60%) as eluent
  8. distillationDistillation under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a6db91919c714284aa39326dd7778a41
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255496B1

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