Acetonitrile → HCID 69215011, compound

HRID 2221856Notes

Reaction equation

HRID 2221856 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:44])=[C:9]([CH2:11][O:12][C:13]2[CH:41]=[CH:40][C:16]([CH2:17][O:18][C:19]3[C:23](/[CH:24]=[CH:25]/[P:26](=[O:33])([O:30]CC)[O:27]CC)=[CH:22][N:21]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:20]=3)=[CH:15][C:14]=2[O:42][CH3:43])[N:10]=1.C(#N)C.C[Si](Br)(C)C>O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:44])=[C:9]([CH2:11][O:12][C:13]2[CH:41]=[CH:40][C:16]([CH2:17][O:18][C:19]3[C:23](/[CH:24]=[CH:25]/[P:26](=[O:27])([OH:33])[OH:30])=[CH:22][N:21]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[N:20]=3)=[CH:15][C:14]=2[O:42][CH3:43])[N:10]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 76113Bromotrimethylsilane2×HCID 86605811HCID 86605811, compound

Product 1

HCID 69215011HCID 69215011, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of diethyl (E)-2-{3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}ethenylphosphonate (0.40 g) and acetonitrile (20 mL) was added trimethylsilyl bromide (0.40 g) at room temperature. After stirring the reaction mixture at room temperature for 1 hr, trimethylsilyl bromide (0.30 g) was added again, and the mixture was further stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give (E)-2-{3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}ethenylphosphonic acid as pale-yellow crystals (0.28 g, yield 76%). Recrystallization from tetrahydrofuran-hexane gave pale-yellow prism crystals. melting point: 138-140° C.

Workup

  1. stirringthe mixture was further stirred for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f8fda8ad897b48bc84ab8710b0cb9ea8
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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