Hydrochloric Acid → HCID 86639397, compound

HRID 2420661Notes

Reaction equation

HRID 2420661 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12](F)[C:11]([F:15])=[CH:10][C:3]=1[C:4]([O:6][CH2:7][C:8]#[CH:9])=[O:5].[CH2:16]([OH:19])[C:17]#[CH:18].[H-].[Na+].Cl>CN(C=O)C>[Cl:1][C:2]1[CH:13]=[C:12]([O:19][CH2:16][C:17]#[CH:18])[C:11]([F:15])=[CH:10][C:3]=1[C:4]([O:6][CH2:7][C:8]#[CH:9])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 86639398HCID 86639398, compound

Product 1

HCID 86639397HCID 86639397, compoundYield 129.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 150 ml of DMF, 12.7 g of 2-propynyl 2-chloro-4,5-difluorobenzoate and 3.4 g of propargyl alcohol was added 2.4 g of 60% sodium hydride (oily) under ice-cooling. The reaction mixture was stirred at room temperature overnight. Hydrochloric acid was added to the reaction mixture, followed by extraction with ethyl acetate. The resulting organic layer was washed sequentially with water and an aqueous saturated sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and 19 g of 2-propynyl 2-chloro-5-fluoro-4-(2-propynyloxy)benzoate was obtained.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe resulting organic layer was washed sequentially with water
  4. dry with materialan aqueous saturated sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-571f4d34c8304b598c2024cb4a364457
Source dataset
uspto-grants-2011_06
Patent number
US07956010B2

Reaction notes

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