HCID 53903064, compound → HCID 17804063, compound

HRID 1651830Notes

Reaction equation

HRID 1651830 reaction equation
[OH:1][CH:2]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:3]#[C:4][C:5]([O:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])=[O:6]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([C:2]([C:3]#[C:4][C:5]([O:7][CH2:8][CH:9]=[C:10]([CH3:11])[CH3:12])=[O:6])=[O:1])=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 53903064HCID 53903064, compound

Product 1

HCID 17804063HCID 17804063, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 10.7 g (39 mmol) of 3-methyl-2-butenyl 4-hydroxy-4-(4-methoxyphenyl)-2-butynoate in 150 ml of methylene chloride was added dropwise at 0° to a suspension of 101.7 g (1.17 mol) of manganese dioxide in 200 ml of methylene chloride. The reaction mixture was stirred at 0° for 1 hour, filtered over magnesium sulphate and concentrated. The residue was purified by flash chromatography on 700 g of silica gel (elution agent methylene chloride/ether 4:1). There was obtained 3-methyl-2-butenyl 3-(4-methoxybenzoyl)propiolate as a yellow oil.

Workup

  1. filtrationfiltered over magnesium sulphate
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography on 700 g of silica gel (elution agent methylene chloride/ether 4:1)

Sources & evidence

ORD record
ord-1afec7eff12f424e95924235a8a52568
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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