2,6-Dimethylphenol → Oxazole, 4-[2-(2,6-dimethylphenoxy)ethyl]-5-methyl-2-phenyl-

HRID 479129Notes

Reaction equation

HRID 479129 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].[CH3:10][C:11]1[O:15][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:13][C:12]=1[CH2:22][CH2:23]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH2:23][CH2:22][C:12]1[N:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:15][C:11]=1[CH3:10]

Participants

7

Reactant 4

HCID 113352,6-DimethylphenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanol

Product 1

HCID 18003546Oxazole, 4-[2-(2,6-dimethylphenoxy)ethyl]-5-methyl-2-phenyl-Yield 32.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.1 g of 2,6-Dimethylphenol, 2.01 g of 2-(5-methyl-2-phenyl-oxazole-4yl)-ethanol 2.6 g of triphenylphosphin were dissolved in 30 ml THF and treated at 0° with 1.6 ml DEAD (Diethyl azodicarboxylate). The reaction mixture was kept overnight at RT. Water was added. Twofold extraction with AcOEt, washing with brine, drying over sodium sulfate, and evaporation of the solvents provided a crude product, which was purified by chromatography (SiO2; ether/cyclohexane) to yield 0.89 g of the title compound as a slightly yellow oil.

Workup

  1. extractionTwofold extraction with AcOEt
  2. washwashing with brine
  3. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  4. customprovided a crude product, which
  5. customwas purified by chromatography (SiO2; ether/cyclohexane)

Sources & evidence

ORD record
ord-433b31e76dd5462e96f5d3275faf65de
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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