Acetone → 3-[N-[5-Chloro-3-(alpha-hydroxy-2-chlorobenzyl)-2-thienyl]-N-neopentylcarbamoyl]acrylic acid ethyl ester

HRID 1940196Notes

Reaction equation

HRID 1940196 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH:5]=[CH:6][C:7](=[O:29])[N:8]([C:14]1[S:15][C:16]([Cl:28])=[CH:17][C:18]=1[C:19](=[O:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26])[CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH3:2].[Cl-].[Cl-].[Cl-].[Cs+].[Cs+].[Cs+].[BH4-].[Na+].CC(C)=O>CO>[CH2:1]([O:3][C:4](=[O:30])[CH:5]=[CH:6][C:7](=[O:29])[N:8]([C:14]1[S:15][C:16]([Cl:28])=[CH:17][C:18]=1[CH:19]([OH:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26])[CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH3:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 20975861Cesium trichlorideHCID 702774443-[N-[5-chloro-3-(2-chlorobenzoyl)-2-thienyl]-N-neopentylcarbamoyl]acrylic acid ethyl ester

Product 1

HCID 702775533-[N-[5-Chloro-3-(alpha-hydroxy-2-chlorobenzyl)-2-thienyl]-N-neopentylcarbamoyl]acrylic acid ethyl esterYield 103.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-[N-[5-chloro-3-(2-chlorobenzoyl)-2-thienyl]-N-neopentylcarbamoyl]acrylic acid ethyl ester (2.37 g) and cesium trichloride.heptahydrate (2.98 g) in methanol (100 ml) was gradually added, sodium borohydride (303 mg) at room temperature. The mixture stirred for 20 minutes at room temperature, to which was added acetone, then the solvent was distilled off. To the residue were added 1M potassium hydrogensulfate and acetic acid ethyl ester. The organic layer was washed with a saturated aqueous saline solution, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by means of a silica-gel column chromatography to give a non-crystalline solid (2.47 g).

Workup

  1. customat room temperature
  2. distillationthe solvent was distilled off
  3. additionTo the residue were added 1M potassium hydrogensulfate and acetic acid ethyl ester
  4. washThe organic layer was washed with a saturated aqueous saline solution
  5. dry with materialby drying over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by means of a silica-gel column chromatography

Sources & evidence

ORD record
ord-90c17bfe0b3a43ccac691f5f5ec84f75
Source dataset
uspto-grants-1997_12
Patent number
US05698691

Reaction notes

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