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Ethyl Acetate → Methyl (4'-methoxy-3'-oxiranylmethoxybiphenyl-3-yl)acetate

HRID 2247443
Notes
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Reaction equation

HRID 2247443 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[F-].[Cs+].C(=O)([O-])[O-].[K+].[K+].[C:29]([O:32][CH2:33][CH3:34])(=O)C>CN(C)C=O>[CH3:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:11]=2)=[CH:3][C:2]=1[O:1][CH2:34][CH:33]1[CH2:29][O:32]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 25953Cesium fluorideHCID 59219199Methyl (3'-hydroxy-4'-methoxybiphenyl-3-yl)acetate

Product 1

HCID 59219337Methyl (4'-methoxy-3'-oxiranylmethoxybiphenyl-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

205 mg of Methyl (3′-hydroxy-4′-methoxybiphenyl-3-yl)acetate was dissolved in 3 ml of N,N-dimethylformamide, then 205 mg of glycidyl nocylate, 35 mg of cesium fluoride and 130 mg of potassium carbonate were added thereto, and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate and washed with 1N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography, to give 79 mg of the title compound in the 4:1 hexane-ethyl acetate fraction.

Workup

  1. washwashed with 1N hydrochloric acid
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-38960115178345598dccf2a57192c628
Source dataset
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07687664B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes