Sodium Hydroxide → HCID 53943264, compound

HRID 257623Notes

Reaction equation

HRID 257623 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH:26]=[CH: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]([CH:26]=[CH: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 54483512HCID 54483512, compound

Product 1

HCID 53943264HCID 53943264, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 3-[3-[2-(4,5-diphenyl-2-oxazolyl)ethyl]phenyl]-2-propenoate (1.50 g, 3.5 mmol), 3N sodium hydroxide solution (3.5 mL) and methanol (100 mL) was heated on a steam bath. After 25 minutes the mixture was cooled, concentrated, diluted with water and made pH=1 with dilute hydrochloric acid solution. The mixture was extracted three times with CH2Cl2. The combined extracts were washed with saturated NaCl solution, dried over sodium sulfate and the solvent evaporated. The residual oil was chromatographed on a column of silica gel using a mixture of chloroform and methanol (9:1) as eluent to give 3-[3-[2-(4,5-diphenyl-2-oxazolyl)ethyl]phenyl]-2-propenoic acid (1.40 g, 100%) as the hydrated hexane solvate after recrystallization from a mixture of hexanes and CH2Cl2 (3:1), mp 114°-115° C.

Workup

  1. temperaturewas heated on a steam bath
  2. temperatureAfter 25 minutes the mixture was cooled
  3. concentrationconcentrated
  4. additiondiluted with water
  5. extractionThe mixture was extracted three times with CH2Cl2
  6. washThe combined extracts were washed with saturated NaCl solution
  7. dry with materialdried over sodium sulfate
  8. customthe solvent evaporated
  9. customThe residual oil was chromatographed on a column of silica gel using
  10. additiona mixture of chloroform and methanol (9:1) as eluent

Sources & evidence

ORD record
ord-0dd93754756046209c767afcd87b1457
Source dataset
uspto-grants-1993_11
Patent number
US05262540

Reaction notes

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