Tributylphosphine → ethyl 1-benzyl-3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-2-methoxybenzyl)oxy]-1H-pyrazole-4-carboxylate

HRID 2221766Notes

Reaction equation

HRID 2221766 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:23])=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][OH:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[N:10]=1.C(P(CCCC)CCCC)CCC.[CH2:37]([N:44]1[CH:48]=[C:47]([C:49]([O:51][CH2:52][CH3:53])=[O:50])[C:46](O)=[N:45]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH2:37]([N:44]1[CH:48]=[C:47]([C:49]([O:51][CH2:52][CH3:53])=[O:50])[C:46]([O:20][CH2:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:9]3[N:10]=[C:6]([C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)[O:7][C:8]=3[CH3:23])=[CH:14][C:15]=2[O:21][CH3:22])=[N:45]1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 69217781(4-{[2-(2-Furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-2-methoxyphenyl)methanolHCID 178469738HCID 178469738, compound

Product 1

HCID 69217694ethyl 1-benzyl-3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-2-methoxybenzyl)oxy]-1H-pyrazole-4-carboxylateYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-2-methoxyphenyl)methanol (1.04 g), tributylphosphine (1.34 g), ethyl 1-benzyl-3-hydroxy-1H-pyrazole-4-carboxylate (0.81 g) and tetrahydrofuran (100 mL) was added 1,1′-(azodicarbonyl)dipiperidine (1.67 g) 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 ethyl 1-benzyl-3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-2-methoxybenzyl)oxy]-1H-pyrazole-4-carboxylate as crystals (0.41 g, yield 23%) from a fraction eluted with tetrahydrofuran-hexane (1:2, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 137-138° C.

Workup

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

Sources & evidence

ORD record
ord-3dad18970ba74cab8e488d97538fcf64
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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