Water → (RS)-2-(2-buten-1-yl)-6-tert-butyl-1-indanone

HRID 264487Notes

Reaction equation

HRID 264487 reaction equation
[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][C:11]2=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:15][CH:16](O)[CH:17]=[CH2:18].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>COC(OC)(C)C>[CH2:15]([CH:10]1[CH2:9][C:8]2[C:12](=[CH:13][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=2)[C:11]1=[O:14])[CH:16]=[CH:17][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 184028836-tert-butyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 53952129(RS)-2-(2-buten-1-yl)-6-tert-butyl-1-indanoneYield 53%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

A solution of 11.0 g of 6-tert-butyl-1-indanone, 12.5 ml of 3-buten-2-ol and 110 mg of p-toluenesulfonic acid in 110 ml of 2,2-dimethoxy-propane was boiled under reflux for 41 hours on a water separator filled with molecular sieve (0.4 nm, 2 mm pearl shaped). The reaction mixture was subsequently concentrated in a vacuum and purified by column chromatography on silica gel (hexane/diethyl ether 6:1). 7.35 g (53%) of (RS)-2-(2-buten-1-yl)-6-tert-butyl-1-indanone was obtained as a yellow oil.

Workup

  1. additionseparator filled with molecular sieve (0.4 nm, 2 mm pearl shaped)
  2. concentrationThe reaction mixture was subsequently concentrated in a vacuum
  3. custompurified by column chromatography on silica gel (hexane/diethyl ether 6:1)

Sources & evidence

ORD record
ord-7bc9973b1e09494ab18106a24a1e1157
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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