Triphenylphosphine → t-Butoxycarbonylamino-3-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene

HRID 325032

Reaktionsgleichung

Reaktionsgleichung von HRID 325032
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[C:32]([O:36][C:37]([NH:39][C:40]1[C:41]([CH3:47])=[C:42]([OH:46])[CH:43]=[CH:44][CH:45]=1)=[O:38])([CH3:35])([CH3:34])[CH3:33].[C:48]([C:50]1[CH:55]=[CH:54][C:53]([CH2:56][CH2:57]O)=[CH:52][CH:51]=1)#[N:49]>C1COCC1.O>[C:32]([O:36][C:37]([NH:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([O:46][CH2:57][CH2:56][C:53]2[CH:54]=[CH:55][C:50]([C:48]#[N:49])=[CH:51][CH:52]=2)[C:41]=1[CH3:47])=[O:38])([CH3:35])([CH3:34])[CH3:33]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 28008154-(2-Hydroxyethyl)benzonitrileHCID 5462977Diethyl azodicarboxylateHCID 220334873-t-Butoxycarbonylamino-2-methylphenol

Produkt 1

HCID 22033517t-Butoxycarbonylamino-3-[2-(4-cyanophenyl)ethoxy]-2-methylbenzeneAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Triphenylphosphine (1.31 g, 13.5 mmol) and diethylazodicarboxylate (1.7 mL) were dissolved in THF (20 mL) under nitrogen. After 15 minutes 3-t-butoxycarbonylamino-2-methylphenol (2.48 g; 11.1 mmol; from step (i) above) dissolved in THF (20 mL) and 2-(4-cyanophenyl)ethanol (1.9 g, 13 mmol) were added. After 5 days at room temperature water was added and the stirring continued for 30 minutes. The mixture was extracted with EtOAc. The organic phase was washed with water and brine, dried (MgSO4) and the solvent removed in vacuo. Purification by flash chromatography afforded 2.98 g (77%) of the sub-title compound.

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7b47ae80fd18405c948537f60313a90d
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06221898B1

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