MeOH tetrahydrofuran → HCID 58477273, compound

HRID 876529Notes

Reaction equation

HRID 876529 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[OH:7][C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[CH:10][C:9]=1[C:17](=[O:28])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1SC.[CH2:29]1COCC1.CO>O>[OH:7][C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[CH:10][C:9]=1[C:17](=[O:28])/[CH:18]=[CH:19]/[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=1[S:3]([CH3:29])(=[O:5])=[O:2]

Participants

5

Reactant 3

HCID 21899815MeOH tetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 58477331HCID 58477331, compound

Product 1

HCID 58477273HCID 58477273, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of OXONE (3.7 g, 6 mmol) in H2O (15 ml) was added drop wise to a solution of (E)-1-(2-hydroxy-3-nitrophenyl)-3-(2-(methylthio)phenyl)prop-2-en-1-one 15 (315 mg, 1.0 mmol) in THF/MeOH (35 mL, 1:1) at room temperature. The reaction mixture was stirred for 12 h. The volatiles were removed under reduced pressure and the resulting precipitate was collected by filtration, rinsed with H2O and dried under vacuum. The crude residue was purified by flash chromatography eluting with CH2Cl2/MeOH (0-1%) to give 16 as a yellow solid (200 mg, yield 58%).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. filtrationthe resulting precipitate was collected by filtration
  3. washrinsed with H2O
  4. customdried under vacuum
  5. customThe crude residue was purified by flash chromatography
  6. washeluting with CH2Cl2/MeOH (0-1%)

Sources & evidence

ORD record
ord-9cb13cec3d574972a90e2de7e6ff9545
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

Loading…