p-Toluenesulfonic acid monohydrate → HCID 59216307, compound

HRID 2245988Notes

Reaction equation

HRID 2245988 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([C:12](=[O:15])[CH:13]=[O:14])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([O-])([O-])[O:17][CH2:18][CH3:19].O.[C:23]1(C)C=CC(S(O)(=O)=O)=C[CH:24]=1>C1(C)C=CC=CC=1>[CH2:23]([O:14][CH:13]([O:17][CH2:18][CH3:19])[C:12]([C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([F:1])[CH:11]=1)=[O:15])[CH3:24]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 53630039EthylorthoformateHCID 59216303Methyl 2-fluoro-4-(oxoacetyl)benzoate

Product 1

HCID 59216307HCID 59216307, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 2-fluoro-4-(oxoacetyl)benzoate (1.60 g), ethyl orthoformate (5.2 mL), p-toluenesulfonic acid monohydrate (70 mg) in toluene (20 mL) was heated under reflux for 3 h. After cooling, the mixture was concentrated. The residue was flash chromatographed on a silica gel column to give the desired product (0.63 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated
  5. customchromatographed on a silica gel column

Sources & evidence

ORD record
ord-283b82834f9b4ad7907454b399b6f013
Source dataset
uspto-grants-2010_03
Patent number
US07683060B2

Reaction notes

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