Triphenylphosphine → Ethyl [5-{5-(4-methoxy-3-propylphenyl)pentyloxy}-1-naphthalenyloxy]acetate

HRID 463340

Reaktionsgleichung

Reaktionsgleichung von HRID 463340
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:5][C:4]=1[CH2:15][CH2:16][CH3:17].O[C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH:21]=[CH:22][CH:23]=[C:24]2[O:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:19]2[CH:28]=[CH:27][CH:26]=[C:25]3[C:20]=2[CH:21]=[CH:22][CH:23]=[C:24]3[O:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:5][C:4]=1[CH2:15][CH2:16][CH3:17]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 202829315-(4-Methoxy-3-propylphenyl)pentanolHCID 20475151Ethyl(5-hydroxy-1-naphthalenyloxy)acetate

Produkt 1

HCID 54574782Ethyl [5-{5-(4-methoxy-3-propylphenyl)pentyloxy}-1-naphthalenyloxy]acetateAusbeute 79,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred suspension of 5-(4-methoxy-3-propylphenyl)pentanol (2.48 g), ethyl (5-hydroxy-1-naphthalenyloxy)acetate (2 g), and triphenylphosphine (3.2 g) in dry tetrahydrofuran (30 ml) under nitrogen was added diethyl azodicarboxylate (1.65 ml) slowly so that the temperature did not rise above 50°. After 3 hours the solution was evaporated, and the residue was chromatographed on silica with a mixture of dichloromethane and light petroleum (bp 40°-60°) (4:6) to give the sub-title ester (3 g), mp 70° (from ethanol).

Aufarbeitung

  1. customdid not rise above 50°
  2. customAfter 3 hours the solution was evaporated
  3. customthe residue was chromatographed on silica with a mixture of dichloromethane and light petroleum (bp 40°-60°) (4:6)

Quellen und Nachweise

ORD-Eintrag
ord-ebc4e97402b44fd087f7b97509c1aa7e
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04518612

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