Triphenylphosphine → HCID 22949960, Verbindung

HRID 1383945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383945
[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.[CH2:14]([S:26][CH2:27][CH2:28]O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1C=CC=CC=1.C(OCC)(=O)C>[CH3:13][O:12][C:10](=[O:11])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:28][CH2:27][S:26][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:7][CH:6]=1

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 73835Ethanol, 2-(dodecylthio)-HCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Produkt 1

HCID 22949960HCID 22949960, VerbindungAusbeute 84,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of methyl 3-[4-hydroxyphenyl)propionate (2.46 g, 13.6 mmol), 2-(dodecylthio)ethanol (3.40 g, 13.7 mmol) and triphenylphosphine (3.60 g, 13.8 mmol) in dry benzene (50 ml) was treated at 22° C. with diethyl azodicarboxylate (2.43 g, 13.9 mmol) added dropwise over 10 min. After 3 h at 22° C., the reaction mixture was diluted with ethyl acetate, washed with water, brine and dried (magnesium sulfate). Evaporation under reduced pressure gave an oil which was triturated with hexane to precipitate the triphenylphosphine oxide and the hydrazine side products. The filtrate was chromatographed on silica gel using a gradient of ethyl acetate (0-5%) in hexane as eluent to give 4.70 g(84%) of 3-[4-[2-(dodecylthio)ethoxy]phenyl]propanoic acid methyl ester as a white solid. Recrystallization from methanol gives white leaflets: m.p. 48° C.

Aufarbeitung

  1. additionadded dropwise over 10 min
  2. washwashed with water, brine
  3. dry with materialdried (magnesium sulfate)
  4. customEvaporation under reduced pressure
  5. customgave an oil which
  6. customwas triturated with hexane
  7. customto precipitate the triphenylphosphine oxide
  8. customThe filtrate was chromatographed on silica gel using a gradient of ethyl acetate (0-5%) in hexane as eluent

Quellen und Nachweise

ORD-Eintrag
ord-1b83877d76e34605aa83046d1adc8dc4
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255496B1

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