Triphenylphosphine → trans-4-[4-(Tert-butoxycarbonyl)phenoxy]-2-butene

HRID 584151

Reaktionsgleichung

Reaktionsgleichung von HRID 584151
[OH:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH2:15](O)[CH:16]=[CH:17][CH3:18].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>C1C=CC=CC=1>[C:9]([O:8][C:6]([C:5]1[CH:13]=[CH:14][C:2]([O:1][CH2:15]/[CH:16]=[CH:17]/[CH3:18])=[CH:3][CH:4]=1)=[O:7])([CH3:10])([CH3:11])[CH3:12]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 200242-Buten-1-olHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 117640tert-Butyl 4-hydroxybenzoate

Produkt 1

HCID 22345517trans-4-[4-(Tert-butoxycarbonyl)phenoxy]-2-buteneAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

A solution of 1,1-dimethylethyl 4-hydroxybenzoate (3.68 g, 18.9 mol) and 2-buten-1-ol (1.37 g, 18.9 mol) in dry benzene (100 ml) at 22° C. was treated with triphenylphosphine (5.48 g, 20.9 mmol) followed by a solution of diisopropyl azodicarboxylate (4.22 g, 20.9 mmol) in dry benzene (10 ml) added dropwise over 7 minutes. After 3 hours at 22° C., the solvent was concentrated under reduced pressure and the residue was chromatographed on silica gel. Elution with a mixture of toluene and ethyl acetate (99:1) gave 3.70 g (79%) of the title material as a clear oil: bp 85-90° C./0.1 torr (bulb to bulb, air bath temperature).

Aufarbeitung

  1. additionadded dropwise over 7 minutes
  2. concentrationthe solvent was concentrated under reduced pressure
  3. customthe residue was chromatographed on silica gel
  4. washElution
  5. additionwith a mixture of toluene and ethyl acetate (99:1)

Quellen und Nachweise

ORD-Eintrag
ord-4c3d187908bb4c528322e43b18d1e4ef
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924391B2

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