Sodium Carbonate → HCID 59464778, Verbindung

HRID 1714588

Reaktionsgleichung

Reaktionsgleichung von HRID 1714588
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:23]=[CH:22][C:19]([CH:20]=O)=[C:18]([Cl:24])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OP([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])(OCC)=O)C.C(=O)(O)[O-].[K+].C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Na+].[Na+]>O.CS(C)=O.CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:23]=[CH:22][C:19]([CH:20]=[CH:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:18]([Cl:24])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

10

Edukt 6

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 13345Triethyl phosphonoacetateHCID 516892Sodium BicarbonateHCID 516893Potassium BicarbonateHCID 166554054-(3-Benzyloxyphenylthio)-2-chlorobenzaldehyde

Produkt 1

HCID 59464778HCID 59464778, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-(3-benzyloxyphenylthio)-2-chlorobenzaldehyde (1) and ethyl diethylphosphonoacetate (2) is stirred for 3 to 8 hours at 50 to 80° C. in an organic solvent, such as dimethylformamide or dimethylsulfoxide, in the presence of a base, such as potassium bicarbonate, sodium bicarbonate, potassium carbonate or sodium carbonate. Subsequently, the reaction mixture is chilled in an ice water bath while being stirred and water is added. The resulting crystals are collected by filtration and washed with aqueous 2-propanol to give ethyl 3-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]acrylate (3) as crude crystals. This product is dissolved in ethylacetate and the mixture was washed with water. The organic layer is concentrated under reduced pressure to obtain a pale yellow oil. To this product, acetone is added and the mixture is stirred while being chilled to form crystals (Crystal seeds are added when necessary). Water is then added and the mixture is stirred while being chilled. The resulting crystals are collected by filtration and washed with acetone-water. The crystals are then dried at 40° C. or below to give ethyl 3-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]acrylate (3) or a hydrate thereof.

Aufarbeitung

  1. temperatureSubsequently, the reaction mixture is chilled in an ice water bath
  2. filtrationThe resulting crystals are collected by filtration
  3. washwashed with aqueous 2-propanol

Quellen und Nachweise

ORD-Eintrag
ord-4a062d7335ec45b58e606242b48284ca
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795472B2

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