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Methyl Acrylate → Methyl 4-(2-t-butyldimethylsiloxyethyl)cinnamate

HRID 55318
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 55318
[O:1]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[C:18]([O:22][CH3:23])(=[O:21])[CH:19]=[CH2:20].CN(C)CCN(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)Cl>[O:1]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH:20]=[CH:19][C:18]([O:22][CH3:23])=[O:21])=[CH:13][CH:12]=1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]
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Komponenten

7

Edukt 3

HCID 7294Methyl AcrylateHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 23254500[2-(4-Bromophenyl)ethoxy](tert-butyl)dimethylsilane

Produkt 1

HCID 53656808Methyl 4-(2-t-butyldimethylsiloxyethyl)cinnamateAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11776TriphenylphosphineKatalysator
HCID 167845palladium(II) acetateKatalysator
HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 4-(2-t-butyldimethylsiloxyethyl)bromobenzene (1.00 g), methyl acrylate (0.55 g), palladium(II) acetate (0.010 g), triphenylphosphine (0.017 g) and N,N,N',N'-tetramethylethylenediamine (0.48 ml) was heated at 140° C. for 24 hours under an atmosphere of argon. To the reaction mixture was added methylene chloride (30 ml), the formed insoluble materials were removed by filtration through a celite column, and the filtrate was concentrated under reduced pressure. To the residue was added diethyl ether (30 ml), and the formed insoluble materials were removed by filtration through a celite column. The filtrate was concentrated to dryness to give methyl 4-(2-t-butyldimethylsiloxyethyl)cinnamate (0.94 g) as a brown oily liquid.

Aufarbeitung

  1. customthe formed insoluble materials were removed by filtration through a celite column
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue was added diethyl ether (30 ml)
  4. customthe formed insoluble materials were removed by filtration through a celite column
  5. concentrationThe filtrate was concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-e247632268cd47b280d1c37682a44f4b
Quelldatensatz
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05624948

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