Tributylphosphine → HCID 17861329, compound

HRID 1294196Notes

Reaction equation

HRID 1294196 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][CH2:14][OH:15].O[C:17]1[CH:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[O:19][N:18]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[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][CH2:14][O:15][C:17]1[CH:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[O:19][N:18]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanolHCID 178498603HCID 178498603, compound

Product 1

HCID 17861329HCID 17861329, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 2-(5-methyl-2-phenyl-4-oxazolyl)ethanol (5.64 g), methyl 3-hydroxy-5-isoxazolecarboxylate (8.00 g), tributylphosphine (15.9 g) and tetrahydrofuran (200 mL) was added a solution (100 mL) of 1,1′-(azodicarbonyl)dipiperidine (19.9 g) in tetrahydrofuran at room temperature and the mixture was stirred for 15 hrs. The precipitated crystals were removed by filtration and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to give crystals (9.50 g, 73%) of methyl 3-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-isoxazolecarboxylate from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 90-91° C.

Workup

  1. customThe precipitated crystals were removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2c26959794c44fc3a8d9207f73310a93
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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