Water → HCID 54039226, compound

HRID 264507Notes

Reaction equation

HRID 264507 reaction equation
[S:1]([O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][CH2:11][C:12]2=[O:15])=[CH:8][CH:7]=1)([CH3:4])(=[O:3])=[O:2].[CH3:16][CH:17](O)[CH:18]=[CH2:19].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>COC(OC)(C)C>[CH2:16]([CH:11]1[CH2:10][C:9]2[C:13](=[CH:14][C:6]([O:5][S:1]([CH3:4])(=[O:2])=[O:3])=[CH:7][CH:8]=2)[C:12]1=[O:15])[CH:17]=[CH:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 19036538HCID 19036538, compound

Product 1

HCID 54039226HCID 54039226, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

A solution of 18.3 g of 6-mesyloxy-1-indanone, 16.7 ml of 3-buten-2-ol and 300 mg of p-toluenesulfonic acid in 400 ml of 2,2-dimethoxy-propane was boiled under reflux for 46 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 4:1). In addition to 8.31 g of educt, there were obtained 11.3 g (50%) of (RS)-2-(2-buten-1-yl)-6-mesyloxy-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 4:1)
  4. additionIn addition to 8.31 g of educt

Sources & evidence

ORD record
ord-7902a12c9ee64ddcb9f2ceb0b6b04ef3
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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