Triphenylphosphine → HCID 68886353, compound

HRID 1294248Notes

Reaction equation

HRID 1294248 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:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=1.[Cl:23][C:24]1[CH:25]=[CH:26][C:27](O)=[C:28]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:29]=1.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>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([O:22][CH2:21][C:18]2[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:3]3[N:4]=[C:5]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[O:6][C:2]=3[CH3:1])=[CH:20][CH:19]=2)=[C:28]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:29]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 110228074-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcoholHCID 17861402Methyl 2-(5-chloro-2-hydroxyphenyl)acetate

Product 1

HCID 68886353HCID 68886353, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of [4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]phenyl]methanol (1.0 g), methyl 2-(5-chloro-2-hydroxyphenyl)acetate (0.74 g), triphenylphosphine (1.08 g) and tetrahydrofuran (50 mL) was dropwise added a solution (40%, 1.79 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 methyl 2-[5-chloro-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetate as an oil (0.68 g, 42%) from a fraction eluted with ethyl acetate-hexane (1:6, v/v).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-220e6e5f45584529a67ac1f98ce94caf
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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