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Sodium Hydroxide → 2-Methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionic acid

HRID 1994077
Notes
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Reaction equation

HRID 1994077 reaction equation
C[O:2][C:3](=[O:27])[C:4]([CH3:26])([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][C:14]2[N:15]=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:17][C:18]=2[CH3:19])[CH:7]=1)[CH3:5].[OH-].[Na+]>CO.O>[CH3:26][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][C:14]2[N:15]=[C:16]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[O:17][C:18]=2[CH3:19])[CH:7]=1)([CH3:5])[C:3]([OH:27])=[O:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 686760192-Methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionic acid methyl ester

Product 1

HCID 686756732-Methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of the title B compound, 2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionic acid methyl ester (3.45 g, 9.45 mmol) in methanol (30 mL) is added sodium hydroxide (1.51 g, 37.81 mmol) in water (10 mL) at RT. The reaction mixture is stirred at 70° C. for 4 h. The reaction mixture is concentrated, poured into water, the aqueous layer is separated, washed with ethyl acetate twice, acidified with concentrated HCl and extracted three times with ethyl acetate. The combined ethyl acetate extract is dried over magnesium sulfate and concentrated to give 2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionic acid as a white solid.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additionpoured into water
  3. customthe aqueous layer is separated
  4. washwashed with ethyl acetate twice
  5. extractionextracted three times with ethyl acetate
  6. extractionThe combined ethyl acetate extract
  7. dry with materialis dried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-06c929a5838d4b8285a53cb4ea39bf8c
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07652061B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes