Potassium Carbonate → 3-Chlorobenzaldehyde

HRID 840161Notes

Reaction equation

HRID 840161 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](C2ON=C3C=CC(C(C4N(C)C=NC=4)O)=CC=23)=[CH:4][CH:3]=1.[C:25]([O-:28])([O-])=O.[K+].[K+]>O.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[O:28])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 131723158HCID 131723158, compound

Product 1

HCID 114773-Chlorobenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

TiCl3/15% in H2O (200 ml) was added at room temperature to a solution of intermediate (6-c) (38 g) in THF (300 ml). The mixture was stirred at room temperature for 90 minutes. The mixture was poured out on ice, basified with K2CO3, filtered over celite, washed with ethyl acetate and decanted. The organic layer was dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1 and 95/5/0.1), yielding 18.7 g (49%) of (±)-[2-amino-5-[4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]phenyl](3-chlorophenyl)methanone (interm. 6-d).

Workup

  1. additionThe mixture was poured out on ice
  2. filtrationfiltered over celite
  3. washwashed with ethyl acetate
  4. customdecanted
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1 and 95/5/0.1)

Sources & evidence

ORD record
ord-b50820293f714f968177f701c37313fe
Source dataset
uspto-grants-2002_04
Patent number
US06365600B1

Reaction notes

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