Water → ethyl(2E)-3-(2,1-benzisothiazol-4-yl)acrylate

HRID 1639851Notes

Reaction equation

HRID 1639851 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[N:17]1[S:18][CH:19]=[C:20]2[C:25]([CH:26]=O)=[CH:24][CH:23]=[CH:22][C:21]=12.O>O1CCCC1>[N:17]1[S:18][CH:19]=[C:20]2[C:25](/[CH:26]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:24][CH:23]=[CH:22][C:21]=12

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 593346042,1-Benzisothiazole-4-carboxaldehyde

Product 1

HCID 66720661ethyl(2E)-3-(2,1-benzisothiazol-4-yl)acrylateYield 380.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Under nitrogen atmosphere, to a suspension of sodium hydride (60%, 1.16 g, 26.6 mmol) in tetrahydrofuran (30 mL) was added a solution of ethyl diethylphosphonoacetate (4.83 mL, 5.41 mmol) in tetrahydrofuran (10 mL) at 0° C., and the mixture was stirred for 20 min. To the reaction mixture was added a solution of 2,1-benzisothiazole-4-carbaldehyde (3.94 g, 24.1 mmol) in tetrahydrofuran (8.3 mL), and the mixture was warmed to room temperature over 4 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=20/80) to give the title compound (4.80 g, yield 85%).

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=20/80)

Sources & evidence

ORD record
ord-f420c0e651b540bea9a8013e119a4210
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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