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Benzoin → Methyl 4,5-diphenyl-2-oxazoleoctanoate

HRID 257618
Notes
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Reaction equation

HRID 257618 reaction equation
[C:1]1([C:7]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)O)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][O:18][C:19](=[O:30])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27](O)=O.C1([N:37]=C=NC2CCCCC2)CCCCC1.C([O-])(=O)C.[NH4+]>CN(C)C1C=CN=CC=1.O.C(O)(=O)C.ClCCl>[C:11]1([C:9]2[N:37]=[C:27]([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C:19]([O:18][CH3:17])=[O:30])[O:8][C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 8400BenzoinHCID 10868DicyclohexylcarbodiimideHCID 75009Monomethyl azelateHCID 517165Ammonium Acetate

Product 1

HCID 15232721Methyl 4,5-diphenyl-2-oxazoleoctanoateYield 78%

Reagents, catalysts & solvents 4

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 176Acetic AcidSolvent
HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent

Procedure

A mixture of benzoin (6.00 g, 28 mmol), azelaic acid monomethyl ester (7.17 g of 92% pure material, 32 mmol), 1,3-dicyclohexylcarbodiimide (7.00 g, 34 mmol), 4-dimethylaminopyridine (catalytic amount) and dichloromethane (120 mL) was stirred at room temperature. After 16 hours, the mixture was filtered and the solvent evaporated. Ammonium acetate (10.90 g, 141 mmol) and acetic acid (150 mL) were added to the residue and the mixture heated at reflux for 65 minutes before being cooled and diluted with water. The mixture was extracted with diethyl ether, the combined extracts dried over sodium sulfate and concentrated in vacuo. The residual oil was chromatographed on a column of silica gel using a mixture of hexanes and diethyl ether (7:3) as eluent to give methyl 4,5-diphenyl-2-oxazoleoctanoate (8.24 g, 77%) as an oil.

Workup

  1. filtrationthe mixture was filtered
  2. customthe solvent evaporated
  3. temperaturethe mixture heated
  4. temperatureat reflux for 65 minutes
  5. temperaturebefore being cooled
  6. extractionThe mixture was extracted with diethyl ether
  7. dry with materialthe combined extracts dried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residual oil was chromatographed on a column of silica gel using
  10. additiona mixture of hexanes and diethyl ether (7:3) as eluent

Sources & evidence

ORD record
ord-1e7f1509404b4317bcfb630e66fb2d25
Source dataset
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05262540

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes