Water → HCID 53677000, compound

HRID 264494Notes

Reaction equation

HRID 264494 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7]1([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[CH2:6][C:5]2=[O:16].[CH3:17][CH:18](O)[CH:19]=[CH2:20].O>COC(OC)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:17]([CH:6]1[C:5](=[O:16])[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([CH3:1])[CH:3]=2)[C:7]21[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:18]=[CH:19][CH3:20]

Participants

6

Reactant 3

HCID 962WaterHCID 117163-Buten-2-olHCID 19036418HCID 19036418, compound

Product 1

HCID 53677000HCID 53677000, compoundYield 587.7%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 64952,2-DimethoxypropaneSolvent

Procedure

A solution of 2.50 g of 5'-methyl-2',3'-dihydro-spiro[cyclo-hexane-1,1'-[1H]indene]-3'-one, 24.1 ml (280 mol) of 3-buten-2-ol and 250 mg of p-toluenesulfonic acid in 250 ml of 2,2-dimethoxy-propane was boiled under reflux for 88 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 8.4 g of educt, there were obtained 18.4 g (59%) of (RS)-2'-(2-buten-1-yl)-5'-methyl-2',3'-dihydro-spiro[cyclohexane-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/ethyl acetate 6:1)
  4. additionIn addition to 8.4 g of educt

Sources & evidence

ORD record
ord-89e00f029adc467aa5b2390ba3eb0b19
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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