HCID 23050458, compound → HCID 23050490, compound

HRID 1651833Notes

Reaction equation

HRID 1651833 reaction equation
[OH:1][CH:2]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][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]>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][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:20][CH:19]=1

Participants

4

Reactant 1

HCID 23050458HCID 23050458, compound

Product 1

HCID 23050490HCID 23050490, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 9.8 g (32 mmol) of 2-(2-methoxyethoxy)-ethyl 4-hydroxy-4-(4-methoxyphenyl)-2-butynoate in 100 ml of methylene chloride was added dropwise at 0° to a suspension of 83 g (0.95 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-(4-methoxybenzoyl)propiolate as a pale 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-9610c0bb0bf344e5a1a69aae5df98471
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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