Triphenylphosphine → 2-Methyl-2-[2-(4-nitro-phenoxy)-phenoxy]-propionic acid tert-butyl ester

HRID 1796615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1796615
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O[C:38]([CH3:47])([CH3:46])[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40].CCOC(/N=N/C(OCC)=O)=O.C([O-])(=O)C(C)C>C1COCC1>[C:42]([O:41][C:39](=[O:40])[C:38]([CH3:47])([O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][C:7]1[CH:16]=[CH:17][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:46])([CH3:45])([CH3:44])[CH3:43]

Komponenten

7

Edukt 5

HCID 11776Triphenylphosphine2×HCID 118940tert-Butyl 2-hydroxyisobutyrateHCID 165337IsobutyrateHCID 3016048o-(p-Nitrophenoxy)phenolHCID 5462977Diethyl azodicarboxylate2×

Produkt 1

HCID 210251752-Methyl-2-[2-(4-nitro-phenoxy)-phenoxy]-propionic acid tert-butyl esterAusbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 388A (1.70 g, 7.35 mmol) and PPh3 (5.80 g, 22.1 mmol) in anhydrous THF (35 ml) was added t-butyl 2-hydroxyisobutyrate (3.83 ml, 22.1 mmol) followed by DEAD (3.47 ml, 22.1 mmol), the reaction mixture was stirred at rt for 19 h. More reagents PPh3 (1.16 g, 4.41 mmol), isobutyrate (0.77 ml, 4.41 mmol) and DEAD (0.69 ml, 4.41 mmol) were added, and the mixture was stirred for another 50 h, concentrated and purified by silica gel flash column chromatography to afford 388B (2.62 g, 96%) as a light pink crystalline solid (50%-80% CH2Cl2-hexanes).

Aufarbeitung

  1. stirringthe mixture was stirred for another 50 h
  2. concentrationconcentrated
  3. custompurified by silica gel flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7be8e4e7d7ea4c73949608c8f95220e9
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07030112B2

Notizen zur Reaktion

Wird geladen…