Sodium Bicarbonate → HCID 67212370, compound

HRID 473342Notes

Reaction equation

HRID 473342 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:15]=2[Cl:16])[OH:9])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+]>CC(C)=O.[O-2].[Cr+6].[O-2].[O-2]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:15]=2[Cl:16])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 67212218HCID 67212218, compound

Product 1

HCID 67212370HCID 67212370, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Procedure

(4-Chlorophenyl)-(4-chloro-pyridin-3-yl)-methanol (7.57 g, 29.8 mmol) was dissolved in dry acetone (150 mL) and chromium (VI) oxide (8.94 g, 89.4 mmol) was added. The reaction mixture was stirred for 18 h and then poured into sat aq NaHCO3 solution (500 mL) and extracted with DCM (2×500 mL). The combined organic layers were dried (MgSO4) and the solvents were removed in vacuo. The residue was purified by column chromatography (normal phase, 50 g, Strata SI-1, silica gigatube, DCM (600 mL)) to give (4-chlorophenyl)-(4-chloropyridin-3-yl)-methanone (4.88 g, 65.0%) as a yellow oil.

Workup

  1. additionpoured
  2. extractionextracted with DCM (2×500 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. customthe solvents were removed in vacuo
  5. customThe residue was purified by column chromatography (normal phase, 50 g, Strata SI-1, silica gigatube, DCM (600 mL))

Sources & evidence

ORD record
ord-a1a668811acd43cf811bf9e9cd4ccd59
Source dataset
uspto-grants-2014_01
Patent number
US08633318B2

Reaction notes

Loading…