Ethyl cinnamyl carbonate → 1-Phenyl-1-phenoxy-2-propene

HRID 14441Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 14441
[O-:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].C(=O)(O[CH2:14][CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)OCC>>[C:17]1([CH:16]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:15]=[CH2:14])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

3

Edukt 2

HCID 232463Ethyl cinnamyl carbonateHCID 4445035Phenolate Sodium

Produkt 1

HCID 117359621-Phenyl-1-phenoxy-2-propeneAusbeute 81,3 %

Versuchsvorschrift

By the procedure for entry 9 of Table 1, the reaction of sodium phenoxide (232 mg, 2.00 mmol) and ethyl cinnamyl carbonate (192 mg, 0.930 mmol) with [(COD)IrCl]2 (6.7 mg, 0.010 mmol) and L1 (Sa,Sc,Sc) (10.8 mg, 0.0200 mmol) as catalyst was conducted at room temperature for 32 h. 1H NMR analysis of the crude reaction showed the ratios of branched to linear products to be 99/1. After purification, 159 mg of the title compound (75%) was isolated. HPLC analysis as described above indicated that the enantiomeric excess of the major product was 94%.

Aufarbeitung

  1. custom1H NMR analysis of the crude reaction
  2. customAfter purification

Quellen und Nachweise

ORD-Eintrag
ord-cc18da941b554ad5b0897d3daa0d8ff2
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732365B2

Notizen zur Reaktion

Wird geladen…