3-Buten-2-ol → HCID 54483366, compound

HRID 264461Notes

Reaction equation

HRID 264461 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[CH2:7][CH2:6]2.[CH3:15][CH:16](O)[CH:17]=[CH2:18]>COC(OC)(C)C.C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:15]([CH:7]1[CH2:6][C:5]2[C:9](=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:8]1=[O:14])[CH:16]=[CH:17][CH3:18]

Participants

6

Reactant 2

HCID 117163-Buten-2-olHCID 750185,6-Dimethoxy-1-indanone

Product 1

HCID 54483366HCID 54483366, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolventHCID 64952,2-DimethoxypropaneSolvent

Procedure

A solution of 20 g of 5,6-dimethoxy-1-indanone, 21.5 ml (0.25 mol) of 3-buten-2-ol and 200 mg of p-toluenesulfonic acid in 21.5 ml of 2,2-dimethoxypropane and 200 ml of anhydrous toluene was boiled under reflux for 24 hours. The reaction mixture was subsequently concentrated in a vacuum and purified by column chromatography on silica gel (hexane/ethyl acetate 3:2). 6.8 g (27%) of (RS)-2-(2-buten-1-yl)-5,6-dimethoxy-1-indanone were obtained as a yellow oil.

Workup

  1. temperatureunder reflux for 24 hours
  2. concentrationThe reaction mixture was subsequently concentrated in a vacuum
  3. custompurified by column chromatography on silica gel (hexane/ethyl acetate 3:2)

Sources & evidence

ORD record
ord-50b761c09df744ab872e07e9b17024c5
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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