HCID 54523158, compound → HCID 53741148, compound

HRID 1651827Notes

Reaction equation

HRID 1651827 reaction equation
[OH:1][CH:2]([C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[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]>[CH3:24][O:23][C:15]1[CH:14]=[C:13]([CH:18]=[C:17]([O:19][CH3:20])[C:16]=1[O:21][CH3:22])[C:2]([C:3]#[C:4][C:5]([O:7][CH2:8][CH:9]=[C:10]([CH3:11])[CH3:12])=[O:6])=[O:1]

Participants

4

Reactant 1

HCID 54523158HCID 54523158, compound

Product 1

HCID 53741148HCID 53741148, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 10.7 g (32 mmol) of 3-methyl-2-butenyl 4-hydroxy-4-(3,4,5-trimethoxyphenyl)-2-butynoate in 200 ml of methylene chloride was added dropwise at 0° to a suspension of 84 g (0.97 mol) of manganese dioxide in 200 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 500 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1) and crystallized from ether/hexane. There was obtained 3-methyl-2-butenyl 3-(3,4,5-trimethoxybenzoyl)propiolate of melting point 52°-53°.

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)
  4. customcrystallized from ether/hexane

Sources & evidence

ORD record
ord-915c42cd32614e2292922829273b3278
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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