Water → HCID 54561982, compound

HRID 264400Notes

Reaction equation

HRID 264400 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:15][CH3:16])([CH2:13][CH3:14])[CH2:8][C:9]2=[O:12])=[CH:5][CH:4]=1.[CH3:17][CH:18](O)[CH:19]=[CH2:20].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>COC(OC)(C)C>[CH2:17]([CH:8]1[C:7]([CH2:15][CH3:16])([CH2:13][CH3:14])[C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9]1=[O:12])[CH:18]=[CH:19][CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 19036614HCID 19036614, compound

Product 1

HCID 54561982HCID 54561982, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

A solution of 22.0 g of 6-methoxy-3,3-diethyl-1-indanone, 20.8 ml of 3-buten-2-ol and 220 mg of p-toluenesulfonic acid in 220 ml of 2,2-dimethoxypropane was boiled under reflux for 87 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 6:1). In addition to 15.7 g of educt, there were obtained 4.1 g (15%) of (RS)-2-(2-buten-1-yl)-6-methoxy-3,3-diethyl-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 6:1)
  4. additionIn addition to 15.7 g of educt

Sources & evidence

ORD record
ord-853594f8092f406eb1f5d3c1cc1c02ba
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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