Water → HCID 54039918, compound

HRID 264497Notes

Reaction equation

HRID 264497 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7]1([CH2:14][CH2:13][CH2:12][CH2:11]1)[CH2:6][C:5]2=[O:15].[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:6]1[C:5](=[O:15])[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([CH3:1])[CH:3]=2)[C:7]21[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:17]=[CH:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 19036599HCID 19036599, compound

Product 1

HCID 54039918HCID 54039918, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

A solution of 17.0 g of 5'-methyl-2',3'-dihydro-spiro[cyclo-pentane-1,1'-[1H]indene]-3'-one, 17.5 ml of 3-buten-2-ol and 170 mg of p-toluenesulfonic acid in 170 ml of 2,2-dimethoxy-propane was boiled under reflux for 71 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 4:1). In addition to 4.0 g of educt, there were obtained 12.7 g (59%) of (RS)-2'-(2-buten-1-yl)-5'-methyl-2',3'-dihydro-spiro[cyclopentane-1,1'-[1H]indene]-3'-one 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 4:1)
  4. additionIn addition to 4.0 g of educt

Sources & evidence

ORD record
ord-85381df18d5d4f61832f751d3a0c8b3e
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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