Pyridine → HCID 10822547, compound

HRID 1719669Notes

Reaction equation

HRID 1719669 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH:8]=[C:7]([CH2:11]O)[C:6]=2[CH:13]=1.N1C=CC=CC=1.S(Cl)([Cl:22])=O>CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH:8]=[C:7]([CH2:11][Cl:22])[C:6]=2[CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 10750419HCID 10750419, compound

Product 1

HCID 10822547HCID 10822547, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2.86 g of 6-chloro-4-hydroxymethyl-2H-1-benzopyrane in 50 ml of ether is reacted with 2 ml of pyridine. To the resulting mixture are then slowly added dropwise, with cooling by ice/water, 1.71 g of thionylchloride in 10 ml of diethylether. Reaction is continued for 5 hours at room temperature, the mixture poured onto ice/water and the ether phase separated. This is then washed with saturated aqueous NaHCO3 and water, dried over MgSO4 and concentrated by evaporation. The product is used directly for further reaction.

Workup

  1. additionTo the resulting mixture are then slowly added dropwise
  2. customReaction
  3. additionthe mixture poured onto ice/water
  4. customthe ether phase separated
  5. washThis is then washed with saturated aqueous NaHCO3 and water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated by evaporation
  8. customThe product is used directly for further reaction

Sources & evidence

ORD record
ord-bec8d581e1dd44729a2b75b064755d26
Source dataset
uspto-grants-1985_09
Patent number
US04542022

Reaction notes

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