Pyridine → HCID 19609444, compound

HRID 1602036Notes

Reaction equation

HRID 1602036 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([F:14])[CH:6]=1)(=[O:3])[CH3:2].S(Cl)(Cl)=O.N1C=CC=CC=1.[CH3:25][CH:26](O)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>CCOCC>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][CH:26]([CH3:25])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:10])=[C:7]([F:14])[CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 200832-OctanolHCID 24386Thionyl ChlorideHCID 227214164-Acetoxy-2-fluorobenzoic acid

Product 1

HCID 19609444HCID 19609444, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 10.8 g (0.06 mol) of 4-acetoxy-2-fluorobenzoic acid was added 60 ml of thionyl chloride, and the mixture was allowed to react under reflux for 7 hours. Then, excess thionyl chloride was distilled off, and 10 ml of pyridine and 5.3 g (0.0402 mol) of 2-octanol were added dropwise. The resultant mixture was stirred at room temperature for a whole day, and then diluted with 200 ml of ether. An organic layer was washed with dilute hydrochloric acid, with a 1N sodium hydroxide aqueous solution and with water in this order, and dried over magnesium sulfate.

Workup

  1. customto react
  2. temperatureunder reflux for 7 hours
  3. distillationThen, excess thionyl chloride was distilled off
  4. washAn organic layer was washed with dilute hydrochloric acid, with a 1N sodium hydroxide aqueous solution and with water in this order
  5. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-c4717878abf7480aae66633d2b5fd013
Source dataset
uspto-grants-1999_11
Patent number
US05980780

Reaction notes

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