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

HRID 2352405Notes

Reaction equation

HRID 2352405 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

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 dimethyformamide 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).

Workup

  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

Sources & evidence

ORD record
ord-3ef3cb22500c4566a4c9f787a99539b7
Source dataset
uspto-grants-1989_10
Patent number
US04876367

Reaction notes

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