Triphenylphosphine → HCID 68883281, compound

HRID 1294278Notes

Reaction equation

HRID 1294278 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][C:4]=1[O:11][CH2:12][C:13]1[N:14]=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:16][C:17]=1OC.O[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:33][C:34]([O:36]C)=[O:35].[C:38]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1.O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH2:33][C:34]([OH:36])=[O:35])=[CH:5][C:4]=1[O:11][CH2:12][C:13]1[N:14]=[C:15]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[O:16][C:17]=1[CH3:38]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 89719Methyl (2-hydroxyphenyl)acetateHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 68886335HCID 68886335, compound

Product 1

HCID 68883281HCID 68883281, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of [4-methoxy-3-[(5-methoxy-2-phenyl-4-oxazolyl)methoxy]phenyl]methanol (0.95 g), methyl 2-(2-hydroxyphenyl)acetate (0.50 g), triphenylphosphine (0.95 g) and tetrahydrofuran (15 mL) was dropwise added a solution (40%, 1.74 g) of diethyl azodicarboxylate in toluene at room temperature, and the mixture was stirred overnight. The reaction mixture was concentrated and the residue was subjected to silica gel column chromatography to give an oil from a fraction eluted with ethyl acetate-hexane (1:3, v/v). To a mixture of the obtained oil, tetrahydrofuran (10 mL) and ethanol (10 mL) was added a 1N aqueous sodium hydroxide solution (5 mL) and the mixture was stirred overnight at room temperature. The reaction mixture was neutralized with 1N hydrochloric acid (5 mL), extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 2-[2-[4-methoxy-3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetic acid from a fraction eluted with ethyl acetate-hexane (1:1, v/v). Recrystallization with ethanol-hexane gave colorless plate crystals (0.52 g, 37%). melting point: 154-155° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give an oil from a fraction
  3. washeluted with ethyl acetate-hexane (1:3
  4. additionTo a mixture of the obtained oil, tetrahydrofuran (10 mL) and ethanol (10 mL)
  5. additionwas added a 1N aqueous sodium hydroxide solution (5 mL)
  6. stirringthe mixture was stirred overnight at room temperature
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-85751f8b3310401c9b93176941a406ec
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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