Pyridine → HCID 19613967, compound

HRID 1585438Notes

Reaction equation

HRID 1585438 reaction equation
S(Cl)(Cl)=O.[C:5]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11]([F:18])[CH:10]=1)(=[O:7])[CH3:6].N1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCC(O)CC>CCOCC>[C:5]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([O:15][CH:22]([CH2:23][CH3:24])[CH2:21][CH3:20])=[O:14])=[C:11]([F:18])[CH:10]=1)(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 1049PyridineHCID 114283-PentanolHCID 24386Thionyl ChlorideHCID 227214164-Acetoxy-2-fluorobenzoic acid

Product 1

HCID 19613967HCID 19613967, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Thionyl chloride in an amount of 60 ml was added to 11.9 g (0.06 mol) of 4-acetoxy-2-fluorobenzoic acid, and the mixture was allowed to react under reflux for 7 hours. Then, excessive thionyl chloride was distilled off, and then 10 ml of pyridine and 3.5 g (0.0420 mol) of 3-pentanol were dropwise added. After the dropwise addition, the mixture was stirred at room temperature over 1 day and night, and then diluted with 200 ml of ether. An organic layer was consecutively washed with diluted hydrochloric acid, with a 1N sodium hydroxide aqueous solution and with water, and dried over magnesium sulfate. The solvent was distilled off, and the resultant crude end product was purified by silica gel column chromatography using hexane/ethyl acetate as a solvent to give 10.7 g (yield 90%) of the end product.

Workup

  1. customto react
  2. temperatureunder reflux for 7 hours
  3. distillationThen, excessive thionyl chloride was distilled off
  4. additionAfter the dropwise addition
  5. washAn organic layer was consecutively washed with diluted hydrochloric acid, with a 1N sodium hydroxide aqueous solution and with water
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customthe resultant crude end product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0be39033efe94b23bd0dfe76a90312e2
Source dataset
uspto-grants-1999_08
Patent number
US05938973

Reaction notes

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