Acetic Anhydride → 2-Acetoxymethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine

HRID 1444738Notes

Reaction equation

HRID 1444738 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH2:10][C:11]([F:14])([F:13])[F:12])[CH:5]=[CH:4][N+:3]=1[O-].[CH3:16][C:17]([O:19]C(C)=O)=[O:18]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:17]([O:19][CH2:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH2:10][C:11]([F:14])([F:13])[F:12])[CH:5]=[CH:4][N:3]=1)(=[O:18])[CH3:16]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 111720662,3-Dimethyl-4-(2,2,2-trifluoroethoxy)pyridine 1-oxide

Product 1

HCID 231348662-Acetoxymethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridineYield 94%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
92.5 °C

Procedure

40 ml of 2,3-dimethyl-4-(2,2,2-trifluoroethoxy)pyridine N-oxide (0.078 mole) in methylene chloride were dropwise added to a solution of 28.7 ml acetanhydride and 0.182 g 4-dimethylaminopyridine, then methylene chloride was distilled off and the residue was heated to a temperature of from 90 to 95° C. for 4-5 hours. At the end of the reaction, 3.6 ml of water were added and acetic acid was removed by vacuum distillation to obtain an oil product. The yield was 94-96%, determined by HPLC.

Workup

  1. distillationmethylene chloride was distilled off
  2. customAt the end of the reaction, 3.6 ml of water
  3. additionwere added
  4. customacetic acid was removed by vacuum distillation
  5. customto obtain an oil product

Sources & evidence

ORD record
ord-fce8178bd3c44bf89d8d4fe55baef065
Source dataset
uspto-grants-2010_02
Patent number
US07662968B2

Reaction notes

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