3,4-dihydro-2H-pyran → HCID 58905734, compound

HRID 1294078Notes

Reaction equation

HRID 1294078 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 58905734HCID 58905734, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the mixture of 3-fluoro-4-nitrophenol (25 g, 0.160 mol) and 3,4-dihydro-2H-pyran (14 g, 0.167 mol)in dicloromethane (200 ml), pyridinium p-toluenesulfonate (4.0 g, 16 mol) was added portionly under ice-water bath. After overnight at room temperature, the reaction mixture was pored to Si-column chromatography. Eluting by Hexane Ethyl acetate (3:1), the desired product was obtained at 35.5 g (92%) as light yellow solid.

Workup

  1. additionwas added portionly under ice-water bath
  2. washEluting by Hexane Ethyl acetate (3:1)

Sources & evidence

ORD record
ord-2605e35c320743cfa127a2044bd89c82
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

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