Methyl 4-hydroxy-4-(5-indanyl)-2-butynoate → Methyl 3-(5-indanylcarbonyl)propiolate

HRID 1651808Notes

Reaction equation

HRID 1651808 reaction equation
[OH:1][CH:2]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH2:14][CH2:13][CH2:12]2)[C:3]#[C:4][C:5]([O:7][CH3:8])=[O:6]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:14]1[C:15]2[C:11](=[CH:10][C:9]([C:2]([C:3]#[C:4][C:5]([O:7][CH3:8])=[O:6])=[O:1])=[CH:17][CH:16]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 1

HCID 23050455Methyl 4-hydroxy-4-(5-indanyl)-2-butynoate

Product 1

HCID 23050466Methyl 3-(5-indanylcarbonyl)propiolate

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6 g (26 mmol) of methyl 4-hydroxy-4-(5-indanyl)-2-butynoate in 200 ml of methylene chloride was added dropwise at 0° to a suspension of 68 g (0.78 mol) of manganese dioxide in 200 ml of methylene chloride. The reaction mixture was stirred at 0° for 20 minutes, filtered over magnesium sulphate and concentrated. The residue was purified by flash chromatography on 500 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1). There was obtained methyl 3-(5-indanylcarbonyl)propiolate as a yellow oil.

Workup

  1. filtrationfiltered over magnesium sulphate
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography on 500 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-62ed408437014833bd744d9f8b2926f5
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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