Sodium Hydroxide → HCID 10000977, compound

HRID 257629Notes

Reaction equation

HRID 257629 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][O:19][C:20]3[CH:21]=[C:22]([CH2:26][CH2:27][C:28]([O:30]C)=[O:29])[CH:23]=[CH:24][CH:25]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][O:19][C:20]3[CH:21]=[C:22]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH:23]=[CH:24][CH:25]=3)[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10070328Methyl 3-[3-[(4,5-diphenyl-2-oxazolyl)-methoxy]phenyl]propanoate

Product 1

HCID 10000977HCID 10000977, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 3-[3-[(4,5-diphenyl-2-oxazolyl)-methoxy]phenyl]propanoate (6 g, 14.5 mmol), 5N sodium hydroxide solution (8.7 mL) and methanol (150 mL) was heated to reflux on a steam bath. After 20 minutes the mixture was concentrated, diluted with water (200 mL) and 2N hydrochloric acid solution to pH=1. After filtration and drying in air overnight, the solid was recrystallized from a mixture of hexanes and CH2Cl2 to give 3-[3-[(4,5-diphenyl-2-oxazolyl)methoxy]phenyl]propanoic acid (4.15 g, 71%), m.p. 118°-120° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux on a steam bath
  3. concentrationAfter 20 minutes the mixture was concentrated
  4. additiondiluted with water (200 mL) and 2N hydrochloric acid solution to pH=1
  5. filtrationAfter filtration
  6. customdrying in air overnight
  7. customthe solid was recrystallized from a mixture of hexanes and CH2Cl2

Sources & evidence

ORD record
ord-9d2ceafbf19f4b9d856b838c15391359
Source dataset
uspto-grants-1993_11
Patent number
US05262540

Reaction notes

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