HCID 23050481, compound → HCID 23050483, compound

HRID 1651810Notes

Reaction equation

HRID 1651810 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:15])[C:9]#[C:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:9]#[C:10][C:11]([O:13][CH3:14])=[O:12])=[O:15])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 23050481HCID 23050481, compound

Product 1

HCID 23050483HCID 23050483, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7.5 g (36 mmol) of methyl 4-(4-fluorophenyl)-4-hydroxy-2-butynoate in 100 ml of methylene chloride was added dropwise at 0° to a suspension of 89.3 g (1.03 mol) of manganese dioxide in 150 ml of methylene chloride. The reaction mixture was stirred at 0° for 30 minutes filtered over magnesium sulphate and concentrated. Crystallization of the residue from ether/hexane yielded methyl 3-(4-fluorobenzoyl)propiolate of melting point 62°-63°.

Workup

  1. filtrationfiltered over magnesium sulphate
  2. concentrationconcentrated
  3. customCrystallization of the residue from ether/hexane

Sources & evidence

ORD record
ord-297cc64f03f84bc0865c1983ee9d6542
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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