Pyridine → HCID 20502717, compound

HRID 851166Notes

Reaction equation

HRID 851166 reaction equation
N1C=CC=CC=1.[F:7][C:8]1[CH:19]=[CH:18][C:11]2[C:12]([CH2:16]O)=[CH:13][CH2:14][O:15][C:10]=2[CH:9]=1.S(Cl)([Cl:22])=O>C(OCC)C>[F:7][C:8]1[CH:19]=[CH:18][C:11]2[C:12]([CH2:16][Cl:22])=[CH:13][CH2:14][O:15][C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 20502713HCID 20502713, compound

Product 1

HCID 20502717HCID 20502717, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1.22 g of pyridine are added to 28 g of 7-fluoro-4-hydroxymethyl-2H-1-benzopyrane in 50 ml of diethylether. The mixture is cooled to 5° and 2 g of thionylchloride in 10 ml diethylether slowly added dropwise. The reaction is continued for 30 minutes at 5°-10° and 2 hours at room temperature. The resulting mixture is poured onto ice-water, the organic phase separated and the aqueous phase extracted with a further 20 ml of diethyl ether. The combined ether solutions are dried over MgSO4 and concentrated by evaporation.

Workup

  1. temperatureThe mixture is cooled to 5°
  2. additionThe resulting mixture is poured onto ice-water
  3. customthe organic phase separated
  4. extractionthe aqueous phase extracted with a further 20 ml of diethyl ether
  5. dry with materialThe combined ether solutions are dried over MgSO4
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-2b83fe5b628c4e169af0741e593d5c02
Source dataset
uspto-grants-1983_05
Patent number
US04382951

Reaction notes

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