HCID 23050448, compound → HCID 23050450, compound

HRID 1651837Notes

Reaction equation

HRID 1651837 reaction equation
[OH:1][CH:2]([C:15]1[CH:20]=[CH:19][C:18]2[O:21][CH2:22][O:23][C:17]=2[CH:16]=1)[C:3]#[C:4][C:5]([O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14])=[O:6]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:22]1[O:21][C:18]2[CH:19]=[CH:20][C:15]([C:2]([C:3]#[C:4][C:5]([O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14])=[O:6])=[O:1])=[CH:16][C:17]=2[O:23]1

Participants

4

Reactant 1

HCID 23050448HCID 23050448, compound

Product 1

HCID 23050450HCID 23050450, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7.9 g (24.5 mmol) of 2-(2-methoxyethoxy)ethyl 4-hydroxy-4-[3,4-(methylenedioxy)phenyl]-2butynoate in 100 ml of methylene chloride was added dropwise at 0° to a suspension of 64 g (0.74 mol) of manganese dioxide in 150 ml of methylene chloride. The reaction mixture was stirred at 0° for 2 hours, filtered over magnesium sulphate and concentrated. The residue was purified by flash chromatography on 800 g of silica gel (elution agent methylene chloride/ether 4:1). There was obtained 2-(2-methoxyethoxy)ethyl 3-[3,4-(methylenedioxy)-benzoyl]propiolate as a yellow oil.

Workup

  1. filtrationfiltered over magnesium sulphate
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography on 800 g of silica gel (elution agent methylene chloride/ether 4:1)

Sources & evidence

ORD record
ord-74fb3f9f03d640a4bc2a43379c9f116b
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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