HCID 23050493, compound → HCID 23050513, compound

HRID 1651844Notes

Reaction equation

HRID 1651844 reaction equation
[OH:1][CH:2]([C:12]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=1)[C:3]#[C:4][CH2:5][O:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:10][C:9]([CH3:11])=[CH:8][CH2:7][O:6][CH2:5][C:4]#[C:3][C:2]([C:12]1[CH:13]=[C:14]([O:22][CH3:23])[C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=1)=[O:1]

Participants

4

Reactant 1

HCID 23050493HCID 23050493, compound

Product 1

HCID 23050513HCID 23050513, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 30 g (93.6 mmol) of 1-hydroxy-4-[(3-methyl-2-butenyl)oxy]-1-(3,4,5-trimethoxyphenyl)-2-butyne in 350 ml of methylene chloride was added dropwise at 0° to a suspension of 122 g (1.4 mol) of manganese dioxide in 500 ml of methylene chloride. The reaction mixture was stirred at 0° for 3 hours, filtered over magnesium sulphate and concentrated. Flash chromatography of the residue on 1000 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1) and subsequent crystallization of the product from ether/hexane yielded 4-[(3-methyl-2-butenyl)oxy]-1-(3,4,5-trimethoxyphenyl)-2-butyn-1-one of melting point 32°.

Workup

  1. filtrationfiltered over magnesium sulphate
  2. concentrationconcentrated
  3. customFlash chromatography of the residue on 1000 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1) and subsequent crystallization of the product from ether/hexane

Sources & evidence

ORD record
ord-196b12b83e194347aaba9059287a469a
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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