Dimethylformamide → HCID 19036396, compound

HRID 264501Notes

Reaction equation

HRID 264501 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[CH:12]1(Br)[CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CC(C)=O.O>[CH:12]1([O:1][C:2]2[CH:10]=[C:9]3[C:5]([CH2:6][CH2:7][C:8]3=[O:11])=[CH:4][CH:3]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 70206596-Hydroxy-1-indanone

Product 1

HCID 19036396HCID 19036396, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 8.0 g of 6-hydroxy-1-indanone, 6.3 ml of cyclopentyl bromide, 16.4 g of potassium carbonate and 10 ml of N,N-dimethylformamide in 100 ml of acetone was heated to 75° for 35 hours. After cooling, the solution was poured into 150 ml of water and extracted twice with 200 ml of ethyl acetate each time. The combined organic phases were washed once with 100 ml of water and once with 100 ml of saturated sodium chloride solution, dried over magnesium sulfate and the solution was concentrated in a vacuum. The crude product was purified by column chromatography on silica gel (hexane/ethyl acetate 3:1). 9.45 g (81%) of 6-cyclopentoxy-1-indanone were obtained as an orange oil which was used directly in the next reaction.

Workup

  1. temperatureAfter cooling
  2. extractionextracted twice with 200 ml of ethyl acetate each time
  3. washThe combined organic phases were washed once with 100 ml of water and once with 100 ml of saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationthe solution was concentrated in a vacuum
  6. customThe crude product was purified by column chromatography on silica gel (hexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-df6fc6784f89470eae85d034823c0225
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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