Triphenylphosphine → Methyl 2-[2-[[5-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-3-pyridyl]methoxy]phenyl]acetate

HRID 1294271Notes

Reaction equation

HRID 1294271 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][OH:22])[CH:18]=[N:19][CH:20]=1.O[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][C:31]([O:33][CH3:34])=[O:32].C1(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][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][O:22][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:18]=[N:19][CH:20]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 89719Methyl (2-hydroxyphenyl)acetateHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178612255-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethanol

Product 1

HCID 68884653Methyl 2-[2-[[5-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-3-pyridyl]methoxy]phenyl]acetateYield 61%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of [5-(5-methyl-2-phenyl-4-oxazolyl)methoxy-3-pyridyl]methanol (1.50 g), methyl 2-(2-hydroxyphenyl)acetate (0.76 g), triphenylphosphine (1.44 g) and tetrahydrofuran (50 mL) was dropwise added a solution (40%, 2.39 g) of diethyl azodicarboxylate in toluene at room temperature, and the mixture was stirred for 15 hrs. The reaction mixture was concentrated and the residue was subjected to silica gel column chromatography to give crude crystals from a fraction eluted with ethyl acetate-hexane (1:1, v/v) which crude crystals were further subjected to silica gel column chromatography to give crystals (1.24 g, 61%) of methyl 2-[2-[[5-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-3-pyridyl]methoxy]phenyl]acetate from a fraction eluted with tetrahydrofuran-hexane (3:2, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 77-78° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give crude crystals from a fraction
  3. washeluted with ethyl acetate-hexane (1:1

Sources & evidence

ORD record
ord-c0484be8f1824d59ac166c6202395496
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

Loading…