1,4-Dioxane → (E)-methyl-2-(2-((4-(2-methoxyethoxy)phenoxy)methyl)-4-chlorophenyl)-3-methoxyacrylate

HRID 1360015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360015
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:23]=[CH:22][C:9]([O:10][CH2:11][C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2B(O)O)=[CH:8][CH:7]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1.[CH3:38][O:39][C:40](=[O:46])/[C:41](/I)=[CH:42]\[O:43][CH3:44]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:38][O:39][C:40](=[O:46])/[C:41](/[C:13]1[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:12]=1[CH2:11][O:10][C:9]1[CH:22]=[CH:23][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:7][CH:8]=1)=[CH:42]/[O:43][CH3:44]

Komponenten

8

Edukt 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 669702642-((4-(2-Methoxyethoxy)phenoxy)methyl)-4-chlorophenylboronic acidHCID 86624615(E)-methyl-2-iodo-3-methoxy-2-propenoate

Produkt 1

HCID 11611173(E)-methyl-2-(2-((4-(2-methoxyethoxy)phenoxy)methyl)-4-chlorophenyl)-3-methoxyacrylateAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

1.1 g (3.3 mmol) of the compound obtained in Step 3, 0.17 g (0.15 mmol) of tetrakis(triphenylphosphine) palladium and 1.96 g (9.0 mmol) of K3PO4 were placed in a flask, and 5 ml of dioxane and 1 ml of water were added thereto. After adding 0.73 g (3.0 mmol) of (E)-methyl-2-iodo-3-methoxy-2-propenoate thereto, the resulting mixture was stirred at 90° C. for 22 hours. The mixture was cooled to room temperature, and 10 ml of ethyl acetate was added thereto. The water layer was separated and extracted twice with 10 ml of ethyl acetate, and the organic layers were combined, washed with 20 ml of water and then with 20 ml of a brine solution, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was subjected to column chromatography using 20% ethyl acetate/hexane as an eluent to obtain 0.87 g (yield 71%) of (E)-methyl-2-(2-((4-(2-methoxyethoxy)phenoxy)methyl)-4-chlorophenyl)-3-methoxyacrylate.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customThe water layer was separated
  3. extractionextracted twice with 10 ml of ethyl acetate
  4. washwashed with 20 ml of water
  5. dry with materialwith 20 ml of a brine solution, dried over anhydrous MgSO4
  6. concentrationconcentrated under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3818a97eb98f46dfbe19fbdbfa4b29db
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879835B2

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