Isopropanol → HCID 53928999, compound

HRID 2082084Notes

Reaction equation

HRID 2082084 reaction equation
[Na].[CH2:2]([O:4][C:5](=[O:24])[CH2:6][C:7]1[O:8][C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1)[CH3:3].[CH:25](O)(C)C>>[CH3:3][CH:2]([O:4][C:5](=[O:24])[CH2:6][C:7]1[O:8][C:9]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1)[CH3:25]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 5360545SodiumHCID 14971801HCID 14971801, compound

Product 1

HCID 53928999HCID 53928999, compoundYield 54%

Procedure

Sodium (80 mg, 3.5 mg atom) was dissolved in isopropanol (21 mL) and ethyl-4,5-diphenyl-2-oxazoleacetate (1.00 g, 3.2 mmol) added. The mixture was heated at reflux for about 1.5 hours, cooled and concentrated. The residue was diluted with water, acidified to pH=2 with 1N HCl solution and extracted with CH2Cl2. The combined extracts were dried over MgSO4, the solvent removed and the residue chromatographed or a column of silica gel. Elution with a mixture of hexanes and EtOAc (9:1) gave the title compound (0.57 g, 54%). IR (film) 1740 cm-1 ; 1H NMR (CDCl3) δ1.26 (6H, d, J=6Hz, CO2CH(CH3)2), 3.89 (2H, s, CH2CO2iPr), 5.08 (1H, septuplet, OCH(CH3)2), 7.25 to 7.40 (6H, m, aromatic H), 7.50 to 7.65 (4H, m, aromatic H); MS m/z 322 (MH+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for about 1.5 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. additionThe residue was diluted with water
  6. extractionextracted with CH2Cl2
  7. dry with materialThe combined extracts were dried over MgSO4
  8. customthe solvent removed
  9. customthe residue chromatographed
  10. washElution
  11. additionwith a mixture of hexanes and EtOAc (9:1)

Sources & evidence

ORD record
ord-509ed8a90afc412abcdffdd394cfc439
Source dataset
uspto-grants-1993_02
Patent number
US05187188

Reaction notes

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