Citric Acid → HCID 68006137, compound

HRID 1026589Notes

Reaction equation

HRID 1026589 reaction equation
[OH:1][CH2:2][CH2:3][C@H:4]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]([O:21]C)=[O:20])=[C:15]([N+:23]([O-:25])=[O:24])[CH:14]=1)[CH3:5].C[Si](C)(C)[O-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[OH:1][CH2:2][CH2:3][C@H:4]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[C:15]([N+:23]([O-:25])=[O:24])[CH:14]=1)[CH3:5]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 23668039Potassium trimethylsilanolateHCID 68006173HCID 68006173, compound

Product 1

HCID 68006137HCID 68006137, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran solution (20.0 ml) of methyl 2′-{[(1R)-3-hydroxy-1-methylpropyl]oxy}-3-nitrobiphenyl-4-carboxylate (793 mg) was added at room temperature potassium trimethylsilanolate (982 mg), followed by stirring for 7 hours. A 10% aqueous citric acid solution was added to the reaction solution, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 2′-{[(1R)-3-hydroxy-1-methylpropyl]oxy}-3-nitrobiphenyl-4-carboxylic acid (761 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fa691f3e4af34cfa9ff8f6058c1f9db3
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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