Trimethyl orthoformate → 3-Chloro-2-(4-chloro-3-dimethoxymethylphenyl)-5-trifluoromethylpyridine

HRID 1957260Notes

Reaction equation

HRID 1957260 reaction equation
[CH:1](OC)([O:4][CH3:5])[O:2][CH3:3].O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3].[Cl:26][C:27]1[C:28]([C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[C:39](C=O)[CH:38]=2)=[N:29][CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1>ClCCl>[Cl:26][C:27]1[C:28]([C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[C:39]([CH:1]([O:4][CH3:5])[O:2][CH3:3])[CH:38]=2)=[N:29][CH:30]=[C:31]([C:33]([F:35])([F:36])[F:34])[CH:32]=1

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 186929322-Chloro-5-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]benzaldehydeHCID 71586775Bentonite

Product 1

HCID 190687453-Chloro-2-(4-chloro-3-dimethoxymethylphenyl)-5-trifluoromethylpyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

50 ml of trimethyl orthoformate were added to 40.0 g of montmorillonite K-10 in 250 ml of anhydrous dichloromethane, after which a solution of 20.0 g of 3-chloro-2-(4-chloro-3-formylphenyl)-5-trifluoromethylpyridine in 50 ml of dichloromethane was added dropwise while stirring and cooling in ice. After stirring at 23° C. for 20 hours, the clay was removed and thoroughly washed with dichloromethane. The dichloromethane phase was concentrated. The residue was purified by chromatography on silica gel with cyclohexane/ethyl acetate (10:1). Yield: 22.1 g (96%) of a colorless oil.

Workup

  1. temperaturecooling in ice
  2. stirringAfter stirring at 23° C. for 20 hours
  3. customthe clay was removed
  4. washthoroughly washed with dichloromethane
  5. concentrationThe dichloromethane phase was concentrated
  6. customThe residue was purified by chromatography on silica gel with cyclohexane/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-0ffccac45b144b839e75b0fdf07c86d6
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Reaction notes

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