Potassium Carbonate → (E)-Ethyl 2-(4-(methoxymethoxy)phenyl)-3-phenylpent-2-enoate

HRID 884049

Reaktionsgleichung

Reaktionsgleichung von HRID 884049
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[C:2]#[C:3][CH2:4][CH3:5].I[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][O:19][CH3:20])=[CH:13][CH:12]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl>[CH3:20][O:19][CH2:18][O:17][C:14]1[CH:15]=[CH:16][C:11](/[C:2](=[C:3](\[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)/[CH2:4][CH3:5])/[C:1]([O:7][CH2:8][CH3:9])=[O:6])=[CH:12][CH:13]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 99169Ethyl pent-2-yn-1-oateHCID 110327301-Iodo-4-(methoxymethoxy)benzene

Produkt 1

HCID 57693046(E)-Ethyl 2-(4-(methoxymethoxy)phenyl)-3-phenylpent-2-enoateAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Versuchsvorschrift

To a mixture of Ethyl 2-pentynoate (5.5 g, 43.6 mmol), 1-iodo-4-(methoxymethoxy)benzene (23.0 g, 87.1 mmol), Phenylboronic acid (10.6 g, 86.9 mmol) in DMF (132 ml) was added a solution of K2CO3 (12.1 g, 87.5 mmol) in H2O (33 ml) under ice cooling, then the mixture was stirred at room temperature for 10 min. PdCl2(PhCN)2 (167 mg, 0.435 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 2 (29%) and the regioisomer (24%). 2: colorless oil; 1H-NMR (CDCl3) δ 1.00 (3H, t, J=7.4), 1.31 (3H, t, J=7.1 Hz), 2.63 (2H, q, J=7.4 Hz), 3.42 (3H, s), 4.28 (2H, q, J=7.1 Hz), 5.07 (2H, s), 6.75 (2H, d, J=8.8 Hz), 6.90 (2H, d, J=8.8 Hz), 7.04 (2H, m), 7.12-7.21 (3H, m); regioisomer: H1-NMR (CDCl3) δ 1.02 (3H, t, J=7.4 Hz), 1.29 (3H, t, J=7.1 Hz), 2.64 (2H, q, J=7.4 Hz), 3.45 (3H, s), 4.27 (2H, q, J=7.1 Hz), 5.10 (2H, s), 6.81 (2H, d, J=8.8 Hz), 6.95 (2H, d, J=8.8 Hz), 7.00 (2H, m), 7.06-7.14 (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-8da65c2fb82145bfbff56050e00c6a0c
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236987B2

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