Tetrahydrofuran → HCID 68488983, compound

HRID 1039253Notes

Reaction equation

HRID 1039253 reaction equation
C[O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])=[N:10][CH:9]=1.C1COCC1.[OH-].[Na+]>CCO>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:11]1[O:12][C:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:21])=[O:2])=[CH:9][N:10]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59167775HCID 59167775, compound

Product 1

HCID 68488983HCID 68488983, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine 5-[2-(2-methoxy-phenyl)-oxazol-5-yl]-pentanoic acid methyl ester (2.1 g, 7.3 mmol) with THF (4 mL), EtOH (4 mL) and 2N NaOH (15 mL) and stir until hydrolysis is complete. Concentrate the mixture, dilute the residue with water and adjust the pH to 3.0-4.0 using aq HCl. Extract the mixture with CH2Cl2 and concentrate the extracts in vacuo. Drying gives 5-[2-(2-methoxy-phenyl)-oxazol-5-yl]-pentanoic acid (1.8 g, 91%). MS (ES): (M+1)+ 274.1, 275.1 m/z.

Workup

  1. concentrationConcentrate the mixture
  2. additiondilute the residue with water
  3. extractionExtract the mixture with CH2Cl2
  4. concentrationconcentrate the extracts in vacuo
  5. customDrying

Sources & evidence

ORD record
ord-b3168055f4c348f9a62a2347cc2e8608
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

Loading…