Ethyl bromoacetate → Methyl [1-methyl-2-[3-(3-thienyl)phenoxy]ethoxy]acetate

HRID 1464774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1464774
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=2)[O:9][CH2:10][CH:11]([OH:13])[CH3:12])=[CH:2]1.S1C=CC(C2C=C(C=CC=2)OCC(=O)C)=C1.S1C=CC(C2C=C(O)C=CC=2)=C1.BrCC(=O)C.C(=O)([O-])[O-].[K+].[K+].[BH4-].[Na+].[H-].[Na+].Br[CH2:61][C:62]([O:64][CH2:65]C)=[O:63]>C(O)C.CN(C)C=O.O.C(OCC)C>[CH3:12][CH:11]([O:13][CH2:61][C:62]([O:64][CH3:65])=[O:63])[CH2:10][O:9][C:8]1[CH:14]=[CH:15][CH:16]=[C:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[CH:7]=1

Komponenten

13

Edukt 8

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 11715BromoacetoneHCID 24758Sodium hydrideHCID 41303433-(Thiophen-3-YL)phenolHCID 4311764Sodium borohydrideHCID 199171261-[3-(3-Thienyl)phenoxy]-2-propanolHCID 199171563-(3-Thienyl)phenoxyacetone

Produkt 1

HCID 53730012Methyl [1-methyl-2-[3-(3-thienyl)phenoxy]ethoxy]acetate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.68 g of 1-[3-(3-thienyl)phenoxy]-2-propanol [synthesized by reducing 3-(3-thienyl)phenoxyacetone, prepared by the reaction of 3-(3-thienyl)phenol and monobromoacetone in the presence of potassium carbonate, with sodium borohydride in ethanol] was dissolved in 7 ml of dimethylformamide, and 48 mg of 60% oily sodium hydride was added. After the mixture was stirred at room temperature for 20 minutes, 0.12 ml of ethyl bromoacetate was added. The mixture was stirred at room temperature for 2 hours, and then ethyl ether and water were added. The organic layer separated was worked up in a customary manner, and the product was purified by silica gel column chromatography [hexane / ethyl acetate=10/1] to give 0.12 g of methyl [1-methyl-2-[3-(3-thienyl)phenoxy]ethoxy]acetate as a colorless oil.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. customThe organic layer separated
  3. customthe product was purified by silica gel column chromatography [hexane / ethyl acetate=10/1]

Quellen und Nachweise

ORD-Eintrag
ord-89ff3ddf0ed8455b9017e2af27830d44
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05306728

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