Methanesulfonyl chloride → 4-Benzyloxy-3-methyl-phenyl-2-methoxy-acrylic acid ethyl ester

HRID 459180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 459180
[CH2:1]([O:3][C:4](=[O:25])[CH:5]([O:23][CH3:24])[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]([CH3:22])[CH:9]=1)O)[CH3:2].S(Cl)(C)(=O)=O>CN(C1C=CN=CC=1)C.ClCCl.CCOCC>[CH2:1]([O:3][C:4](=[O:25])[C:5]([O:23][CH3:24])=[CH:6][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:10]([CH3:22])[CH:9]=1)[CH3:2]

Komponenten

6

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 694224223-(4-Benzyloxy-3-methyl-phenyl)-3-hydroxy-2-methoxy-propionic acid ethyl ester

Produkt 1

HCID 694952094-Benzyloxy-3-methyl-phenyl-2-methoxy-acrylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-(4-Benzyloxy-3-methyl-phenyl)-3-hydroxy-2-methoxy-propionic acid ethyl ester (1 eq), Mesylchloride (1 eq) triethylamine (4 eq) and a catalytic amount of DMAP (0.1 eq) in dichloromethane was stirred at room temperature over night. The reaction mixture was diluted with ether and washed with HCl 1N. Dried and concentrated in vacuo to give a residue which was chromatographed in silica gel to yield the title compound.

Aufarbeitung

  1. washwashed with HCl 1N
  2. customDried
  3. concentrationconcentrated in vacuo
  4. customto give a residue which
  5. customwas chromatographed in silica gel

Quellen und Nachweise

ORD-Eintrag
ord-87afeabfc67d4f01aa96f5e6621454f6
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192982B2

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