Triethyl phosphonoacetate → HCID 69420190, compound

HRID 350169Notes

Reaction equation

HRID 350169 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:48])=[C:9]([CH2:11][O:12][C:13]2[CH:47]=[CH:46][C:16]([CH2:17][N:18]3[CH:22]=[C:21]([CH:23]=O)[C:20]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]5[N:36]=[C:37]([C:41]6[O:42][CH:43]=[CH:44][CH:45]=6)[O:38][C:39]=5[CH3:40])=[CH:29][CH:28]=4)=[N:19]3)=[CH:15][CH:14]=2)[N:10]=1.C(OP([CH2:57][C:58]([O:60][CH2:61][CH3:62])=[O:59])(OCC)=O)C.[H-].[Na+]>CN(C)C=O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:48])=[C:9]([CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:17][N:18]3[CH:22]=[C:21](/[CH:23]=[CH:57]/[C:58]([O:60][CH2:61][CH3:62])=[O:59])[C:20]([O:25][CH2:26][C:27]4[CH:28]=[CH:29][C:30]([O:33][CH2:34][C:35]5[N:36]=[C:37]([C:41]6[O:42][CH:43]=[CH:44][CH:45]=6)[O:38][C:39]=5[CH3:40])=[CH:31][CH:32]=4)=[N:19]3)=[CH:46][CH:47]=2)[N:10]=1

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 86760417HCID 86760417, compound

Product 1

HCID 69420190HCID 69420190, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyl]-3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyloxy]-1H-pyrazol-4-carbaldehyde (14.09 g), ethyl diethylphosphonoacetate (5.88 g), and N,N-dimethylformamide (100 ml), sodium hydride (60%, oily, 1.01 g) was added at 0° C., and the mixture was stirred at room temperature for two hours. The reaction mixture was poured into ice water, and the obtained crystals were collected by filtration, and ethyl(E)-3-[1-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyl]-3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyloxy]-1H-pyrazol-4-yl]propenoate was obtained (13.91 g, yield: 89%). This was recrystallized from ethyl acetate-hexane. Melting point: 138–139° C.

Workup

  1. additionwas added at 0° C.
  2. filtrationthe obtained crystals were collected by filtration

Sources & evidence

ORD record
ord-5ba8a52a1c654d22b1c868fb369fdf24
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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