Diethyl Ether → 5-(3,3-Dimethylbutanoyl)-3-methyl-1,2-di(2-[2-(2-tetrahydropyranyloxy)ethoxy]ethoxy)benzene

HRID 867985Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 867985
[CH3:1][C:2]1[CH:8]=[C:7]([C:9](=[O:15])[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=[C:4]([OH:5])[C:3]=1[OH:16].Cl[CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1.[C:30](=[O:33])([O-])[O-:31].[K+].[K+].[CH2:36]([O:38][CH2:39][CH3:40])[CH3:37]>CN(C)C=O.O>[CH3:14][C:11]([CH3:13])([CH3:12])[CH2:10][C:9]([C:7]1[CH:8]=[C:2]([CH3:1])[C:3]([O:16][CH2:37][CH2:36][O:38][CH2:39][CH2:40][O:31][CH:30]2[CH2:4][CH2:3][CH2:2][CH2:1][O:33]2)=[C:4]([O:5][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH:6]=1)=[O:15]

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 109657372-[2-(2-Chloroethoxy)ethoxy]oxaneHCID 142793123-Methyl-5-(3,3-dimethylbutanoyl)catechol

Produkt 1

HCID 146756075-(3,3-Dimethylbutanoyl)-3-methyl-1,2-di(2-[2-(2-tetrahydropyranyloxy)ethoxy]ethoxy)benzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of 3-methyl-5-(3,3-dimethylbutanoyl)catechol (12 g, 0.054 mole), 2-(2-[2-chloroethoxy]ethoxy)tetrahydropyran (24.8 g, 0.119 mole) and potassium carbonate (16.6 g, 0.12 mole) in 100 ml dimethylformamide was stirred under a nitrogen atmosphere at 140° C. for 16 hours. The reaction mixture was cooled to 25° C. and 500 ml diethyl ether and 300 ml water were added. The layers were separated and the organic layer was washed with four 250 ml portions of water and 100 ml brine, dried over anhydrous magnesium sulfate and the solvent evaporated in vacuo. The resulting brown oil was purified by column chromatography over silica gel with 10% ethyl acetate--90% chloroform. The title compound was isolated as a yellow oil (13.5 g, 44% yield).

Aufarbeitung

  1. customThe layers were separated
  2. washthe organic layer was washed with four 250 ml portions of water and 100 ml brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent evaporated in vacuo
  5. customThe resulting brown oil was purified by column chromatography over silica gel with 10% ethyl acetate--90% chloroform

Quellen und Nachweise

ORD-Eintrag
ord-4cbe639b0b834f0fbe4d477b38d91685
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04777270

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