Water → ethyl (2E)-3-(2-methyl-2H-indazol-4-yl)acrylate

HRID 1639745Notes

Reaction equation

HRID 1639745 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH3:17][N:18]1[CH:26]=[C:25]2[C:20]([CH:21]=[CH:22][CH:23]=[C:24]2[CH:27]=O)=[N:19]1.O>O1CCCC1>[CH3:17][N:18]1[CH:26]=[C:25]2[C:20]([CH:21]=[CH:22][CH:23]=[C:24]2/[CH:27]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 593346182-Methyl-2H-indazole-4-carbaldehyde

Product 1

HCID 66720667ethyl (2E)-3-(2-methyl-2H-indazol-4-yl)acrylateYield 98.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Under nitrogen atmosphere, to a suspension of sodium hydride (1.26 g, 31.5 mmol) in tetrahydrofuran (50 mL) was added a solution of ethyl diethylphosphonoacetate (7.06 g, 31.5 mmol) in tetrahydrofuran (50 mL) at 0° C., and the mixture is was stirred for 20 min. To the reaction mixture was added a solution of 2-methyl-2H-indazole-4-carbaldehyde (4.60 g, 28.7 mmol) in tetrahydrofuran (100 mL), and the mixture was warmed to room temperature over 2 hr. Water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) to give the title compound (6.50 g, yield 98%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-e4cce467a1f74183bef4ce8b8bafa0a8
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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