Methylparaben → 5-Methyl-2-phenyl-4-(2-p-tolyloxy-ethyl)-oxazole

HRID 644008Notes

Reaction equation

HRID 644008 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][C:21]1[O:25][C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:23][C:22]=1[CH2:32][CH2:33][OH:34].O[C:36]1[CH:45]=[CH:44][C:39]([C:40](OC)=O)=[CH:38][CH:37]=1>C1(C)C=CC=CC=1>[CH3:20][C:21]1[O:25][C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:23][C:22]=1[CH2:32][CH2:33][O:34][C:36]1[CH:45]=[CH:44][C:39]([CH3:40])=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanol

Product 1

HCID 205966165-Methyl-2-phenyl-4-(2-p-tolyloxy-ethyl)-oxazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Di-t-butylazodicarboxylate (9.46 g, 41.08 mmol) is added to a stirred solution of triphenylphosphine (10.77 g, 41.08 mmol), 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethanol (7.35 g, 36.15 mmol) and methyl 4-hydroxybenzoate (5.0 g, 32.86 mmol) in toluene (120 mL) at 0° C. After stirring for 15 min, the ice-water bath is removed. Stirring is continued for 1 h at RT, 1 h at 40° C., and overnight at RT. The reaction is then concentrated under vacuum, and the residue is crystallized from EtOAc to give 5-methyl-2-phenyl-4-(2-p-tolyloxy-ethyl)-oxazole as a white solid.

Workup

  1. customthe ice-water bath is removed
  2. stirringStirring
  3. waitis continued for 1 h at RT, 1 h at 40° C.
  4. customovernight
  5. customat RT
  6. concentrationThe reaction is then concentrated under vacuum
  7. customthe residue is crystallized from EtOAc

Sources & evidence

ORD record
ord-d076edfc23aa4e2aa18cf5136802d00a
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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