Water → HCID 54557992, compound

HRID 264388Notes

Reaction equation

HRID 264388 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:13])([CH3:12])[CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[CH3:14][CH:15](O)[CH:16]=[CH2:17].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>COC(OC)(C)C>[CH2:14]([CH:7]1[C:6]([CH3:13])([CH3:12])[C:5]2[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[C:8]1=[O:11])[CH:15]=[CH:16][CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 23293641HCID 23293641, compound

Product 1

HCID 54557992HCID 54557992, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

A solution of 10.0 g of 6-fluoro-3,3-dimethyl-1-indanone, 11.1 ml of 3-buten-2-ol and 200 mg of p-toluenesulfonic acid in 200 ml of 2,2-dimethoxypropane was boiled under reflux for 96 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/ethyl acetate 8:1). In addition to 11.9 g of educt, there were obtained 3.38 g (26%) of (RS)-2-(2-buten-1-yl)-6-fluoro-3,3-dimethyl-1-indanone 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/ethyl acetate 8:1)
  4. additionIn addition to 11.9 g of educt

Sources & evidence

ORD record
ord-c3990a548c4e4f8b973895bb2224a122
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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