Sodium Hydroxide → HCID 10475925, compound

HRID 257625Notes

Reaction equation

HRID 257625 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH2:26][CH2:27][C:28]([O:30]CC)=[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][CH2:19][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:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10320206HCID 10320206, compound

Product 1

HCID 10475925HCID 10475925, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 3-[2-(4,5-diphenyl-2-oxazolyl)ethyl]benzenepropanoate (1.85 g, 4.3 mmol), 3N sodium hydroxide solution (4.4 mL) and methanol (100 mL) was heated on a steam bath. After 20 minutes the mixture was concentrated, diluted with water and 1N hydrochloric acid solution to pH=1 and extracted with CH2Cl2. The combined extracts were dried over sodium sulfate and the solvent evaporated to leave a white solid. Recrystallization from a mixture of hexanes and CH2Cl2 gave 3-[2-(4,5-diphenyl-2-oxazolyl)ethyl]benzenepropanoic acid (1.58 g, 91%) mp 119°-120° C.

Workup

  1. temperaturewas heated on a steam bath
  2. concentrationAfter 20 minutes the mixture was concentrated
  3. additiondiluted with water and 1N hydrochloric acid solution to pH=1
  4. extractionextracted with CH2Cl2
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. customthe solvent evaporated
  7. customto leave a white solid
  8. customRecrystallization
  9. additionfrom a mixture of hexanes and CH2Cl2

Sources & evidence

ORD record
ord-5e09a527b2c0413195f1c264a50e57e0
Source dataset
uspto-grants-1993_11
Patent number
US05262540

Reaction notes

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