Methyl morpholine oxide → 3-(5-Benzyloxy-4-methoxy-2-methylbenzoyl)-2-chloro-4-trifluoromethylpyridine

HRID 1835411Notes

Reaction equation

HRID 1835411 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([O:29][CH3:30])=[CH:11][C:12]([CH3:28])=[C:13]([CH:15]([C:17]2[C:18]([Cl:27])=[N:19][CH:20]=[CH:21][C:22]=2[C:23]([F:26])([F:25])[F:24])[OH:16])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:1]([O:8][C:9]1[C:10]([O:29][CH3:30])=[CH:11][C:12]([CH3:28])=[C:13]([CH:14]=1)[C:15]([C:17]1[C:18]([Cl:27])=[N:19][CH:20]=[CH:21][C:22]=1[C:23]([F:26])([F:24])[F:25])=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 82029Methyl morpholine oxideHCID 12151540(5-Benzyloxy-4-methoxy-2-methylphenyl)(2-chloro-4-trifluoromethyl-3-pyridyl)methanol

Product 1

HCID 121515413-(5-Benzyloxy-4-methoxy-2-methylbenzoyl)-2-chloro-4-trifluoromethylpyridineYield 84%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×HCID 178419074HCID 178419074, compoundSolvent

Procedure

(5-benzyloxy-4-methoxy-2-methylphenyl)(2-chloro-4-trifluoromethyl-3-pyridyl)methanol (5.9 g) was dissolved in a mixed solvent of anhydrous methylene chloride (50 ml) and acetonitrile (5 ml), and tetrapropylammonium perruthenate (95 ml), N-methylmorpholine-N-oxide (2.38 g) and molecular sieve 4A (6.8 g) were sequentially added thereto, followed by stirring in a stream of argon at room temperature for three nights. The reaction mixture was distilled off under reduced pressure, the residue thus obtained was suspended in methylene chloride and subjected to filtration by celite, and the residue was adequately washed with methylene chloride (200 ml). The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 4.93 g (yield 84%) of 3-(5-benzyloxy-4-methoxy-2-methylbenzoyl)-2-chloro-4-trifluoromethylpyridine (compound No. 27; m.p. 116-117° C.), and its structure was confirmed by nuclear magnetic resonance spectrum.

Workup

  1. additionwere sequentially added
  2. distillationThe reaction mixture was distilled off under reduced pressure
  3. customthe residue thus obtained
  4. filtrationsubjected to filtration by celite
  5. washthe residue was adequately washed with methylene chloride (200 ml)
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-93c6d1d2d4d54fa987cdb4da1b78766c
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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