Water → Ethyl (2H-1,3-benzodioxol-5-yl)(oxo)acetate

HRID 1934596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1934596
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH2:2]1.[Cl-].[Cl-].[Cl-].[Al+3].[OH2:14].CCCCCC.[C:21]([O:24][CH2:25][CH3:26])(=[O:23])[CH3:22]>ClCCl>[CH2:25]([O:24][C:21](=[O:23])[C:22]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][O:3][C:4]=2[CH:9]=1)=[O:14])[CH3:26]

Komponenten

7

Edukt 5

HCID 962WaterHCID 8058HexaneHCID 8857Ethyl AcetateHCID 92291,3-BenzodioxoleHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 2758872Ethyl (2H-1,3-benzodioxol-5-yl)(oxo)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of ethyl oxalyl chloride (50 ml, 0.45 mmol) and 1,3-benzodioxole (50 g, 0.41 mmol) in dichloromethane (40 ml) was added dropwise to a stirred slurry of aluminium trichloride (71 g, 0.53 mmol) in dichloromethane (500 ml) at 0° C. under a nitrogen atmosphere. After 2 hours the mixture was poured into iced water and the organic layer was washed with further volumes of water (3×500 ml), saturated sodium bicarbonate solution (500 ml) and brine (500 ml). The organic layer was dried (magnesium sulphate) and concentrated to give an orange oil. Flash column chromatography (90% hexane, 10% ethyl acetate) gave 30 g of the subtitle compound as a pale yellow oil.

Aufarbeitung

  1. washthe organic layer was washed with further volumes of water (3×500 ml), saturated sodium bicarbonate solution (500 ml) and brine (500 ml)
  2. dry with materialThe organic layer was dried (magnesium sulphate)
  3. concentrationconcentrated
  4. customto give an orange oil

Quellen und Nachweise

ORD-Eintrag
ord-b8622bb014b94875ab4d55870c6b58ec
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06384070B2

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