Sodium hydride → Methyl 3-[3-nitro-4-(piperazin-1-yl)phenyl]acrylate

HRID 2378570Notes

Reaction equation

HRID 2378570 reaction equation
[Br-].[CH3:2][O:3][C:4]([CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5].[H-].[Na+].[N+:28]([C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][C:38]=1[N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)[CH:34]=O)([O-:30])=[O:29]>C1COCC1.[Cl-].[Na+].O>[N+:28]([C:31]1[CH:32]=[C:33]([CH:34]=[CH:6][C:4]([O:3][CH3:2])=[O:5])[CH:36]=[CH:37][C:38]=1[N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)([O-:30])=[O:29]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 2733211Phosphonium, (2-methoxy-2-oxoethyl)triphenyl-, bromide (1:1)HCID 607111153-Nitro-4-(piperazin-1-yl)benzaldehyde

Product 1

HCID 68741140Methyl 3-[3-nitro-4-(piperazin-1-yl)phenyl]acrylateYield 74.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of methoxycarbonylmethyl(triphenyl)phosphonium bromide (1.1 g, TCI) in THF (12.5 ml) was added with sodium hydride (115 mg, WAKO) under ice cooling, warmed to room temperature, then added dropwise with a solution of 3-nitro-4-(piperazin-1-yl)benzaldehyde (550.6 mg, MAYB) in THF (12.5 ml), and stirred at the same temperature for 16.5 hours. The reaction mixture was poured into brine (40 ml), and extracted with ethyl acetate (100 ml). The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=5:1) to obtain the title compound (Intermediate Int. n-19, 511 mg).

Workup

  1. extractionextracted with ethyl acetate (100 ml)
  2. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-ac5ac3ea6cf647ec801334b8c52e1dd3
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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