3,4-dihydro-2H-pyran → HCID 10712935, compound

HRID 275988Notes

Reaction equation

HRID 275988 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([CH2:15][CH2:16][OH:17])[CH:12]=[CH:11][C:3]=1[NH:4][C:5](=[O:10])[C:6]([F:9])([F:8])[F:7].[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:14]=[C:13]([CH2:15][CH2:16][O:17][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][O:18]2)[CH:12]=[CH:11][C:3]=1[NH:4][C:5](=[O:10])[C:6]([F:9])([F:7])[F:8]

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10611916HCID 10611916, compound

Product 1

HCID 10712935HCID 10712935, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2′-chloro-4′-(2-hydroxyethyl)-2,2,2-trifluoroacetanilide (1.4 g) and 3,4-dihydro-2H-pyran (1.4 ml) in dichloromethane (15 ml) was added pyridinium p-toluenesulfonate (14 mg), and the mixture was heated under reflux for 1 hour with stirring. After concentration of the reaction mixture in vacuo, the residue was dissolved in ethyl acetate. The solution was washed with a saturated aqueous sodium bicarbonate solution and brine, and dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. Purification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/diethyl ether=3/1) gave 2′-chloro-4′-[2-((RS) -tetrahydropyran-2-yloxy)ethyl]-2,2,2-trifluoroacetanilide (1.4 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. washThe solution was washed with a saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customPurification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/diethyl ether=3/1)

Sources & evidence

ORD record
ord-6b5e24f9581e4cab9b590e24a68ecd0d
Source dataset
uspto-grants-2002_03
Patent number
US06353025B1

Reaction notes

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