Sodium Hydroxide → HCID 67367602, compound

HRID 1910906Notes

Reaction equation

HRID 1910906 reaction equation
[OH-].[Na+].[Si:3]([O:10][CH2:11][C:12]1[N:16]([CH2:17][C:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[O:19])[C:15]([C:27]([O:29]C)=[O:28])=[CH:14][CH:13]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]>O1CCOCC1>[Si:3]([O:10][CH2:11][C:12]1[N:16]([CH2:17][C:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[O:19])[C:15]([C:27]([OH:29])=[O:28])=[CH:14][CH:13]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67366214HCID 67366214, compound

Product 1

HCID 67367602HCID 67367602, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

Aqueous sodium hydroxide solution (1 M, 1.78 mL) was added to a solution of methyl 5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-[2-(4-chlorophenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylate (375 mg, 0.89 mmol) in 1,4-dioxane (10 mL) and stirred at 70° C. for 2 h. The resultant brown solution was cooled to room temperature and concentrated in vacuo to ˜50% of its starting volume. The reaction mixture was acidified to ˜pH 4 by the addition of aqueous HCl (1 M, 1.78 mL) and extracted with EtOAc. The aqueous layer was further extracted with EtOAc (2×10 mL) The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give 5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-[2-(4-chlorophenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylic acid as a brown gum (70% purity, 270 mg, yield ˜95%) The mixture was used without further purification. ESI-MI m/z [M+Na]+ 432.0.

Workup

  1. temperatureThe resultant brown solution was cooled to room temperature
  2. concentrationconcentrated in vacuo to ˜50% of its
  3. additionby the addition of aqueous HCl (1 M, 1.78 mL)
  4. extractionextracted with EtOAc
  5. extractionThe aqueous layer was further extracted with EtOAc (2×10 mL) The combined organic layers
  6. washwere washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e6b5eb2e8c2d492ba281bc7c70c3d03e
Source dataset
uspto-grants-2013_12
Patent number
US08604034B2

Reaction notes

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