Potassium Carbonate → (E)-ethyl 3-cyclopropyl-3-(4-(methoxymethoxy)phenyl)-2-phenylacrylate

HRID 884064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 884064
[CH:1]1([C:4]#[C:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1.I[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][O:20][CH3:21])=[CH:14][CH:13]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.O>[CH:1]1(/[C:4](/[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][O:20][CH3:21])=[CH:14][CH:13]=2)=[C:5](/[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)\[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 639964Ethyl 3-cyclopropylprop-2-ynoateHCID 110327301-Iodo-4-(methoxymethoxy)benzene

Produkt 1

HCID 86630292(E)-ethyl 3-cyclopropyl-3-(4-(methoxymethoxy)phenyl)-2-phenylacrylateAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 498840Bis(benzonitrile)palladium chlorideKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 2 (385 mg, 2.79 mmol), 1-iodo-4-(methoxymethoxy)benzene (1.47 g, 5.57 mmol), Phenylboronic acid (680 mg, 5.58 mmol) and K2CO3 (771 mg, 5.58 mmol) in DMF (8.5 ml)-H2O (2.2 ml) was stirred at room temperature for 10 min. Then PdCl2(PhCN)2 (10.7 mg, 0.0279 mmol) was added under Ar atmosphere, and the mixture was stirred at room temperature for 24 h. The reaction was quenched with H2O under ice cooling, and the whole was extracted with Et2O. The organic layer was washed with H2O, brine, dried over Na2SO4, then concentrated. Purification by silica gel flash column chromatography (eluent: hexane/AcOEt, 30:1 to 10:1) gave 5 (29%). 5: colorless oil; 1H-NMR (CDCl3) δ 0.44 (2H, m), 0.79 (2H, m), 1.29 (3H, t, J=7.2 Hz), 2.30 (1H, m), 3.43 (3H, s), 4.28 (2H, q, J=7.1 Hz), 5.08 (2H, s), 6.78 (2H, d, J=8.8 Hz), 6.85 (2H, d, J=8.8 Hz), 6.99 (2H, m), 7.03-7.09 (3H, m).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 24 h
  2. customThe reaction was quenched with H2O under ice cooling
  3. extractionthe whole was extracted with Et2O
  4. washThe organic layer was washed with H2O, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by silica gel flash column chromatography (eluent: hexane/AcOEt, 30:1 to 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-e8706ccfc7394c62a184e5771b052e4d
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236987B2

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