5-Methoxy-1H-inden-1-one → HCID 14742746, compound

HRID 1651260Notes

Reaction equation

HRID 1651260 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[C:15](=O)[CH:14]=[CH:13]2>O1CCCC1>[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:16]([C:15]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:14][CH2:13]2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 110409905-Methoxy-1H-inden-1-oneHCID 178445865HCID 178445865, compound

Product 1

HCID 14742746HCID 14742746, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of pentyl magnesium bromide (2M; 83 mL) was added with stirring to a chilled (-5° C.) solution of 5-methoxy-1-indenone (24.33 g) in dry tetrahydrofuran (100 mL) and the mixture was stirred at room temperature for 1.5 hours. A few chips of ice were added to destroy excess reagent and after the solvents had been removed under reduced pressure, the residue was taken up in a mixture of dichloromethane (250 mL) and 2N hydrochloric acid and stirred at room temperature for 3 hours. The separated aqueous phase was extracted with dichloromethane (150 mL) then the combined organic layers were dried (MgSO4) and evaporated to provide 30 g of crude product as an oil. Purification of the material by HPLC (dichoromethane-hexane; 2:5) gave 21.62 g of 6-methoxy-3-pentyl-1H-indene as an oil

Workup

  1. stirringthe mixture was stirred at room temperature for 1.5 hours
  2. additionA few chips of ice were added
  3. customto destroy excess reagent
  4. customafter the solvents had been removed under reduced pressure
  5. additionthe residue was taken up in a mixture of dichloromethane (250 mL) and 2N hydrochloric acid
  6. stirringstirred at room temperature for 3 hours
  7. extractionThe separated aqueous phase was extracted with dichloromethane (150 mL)
  8. dry with materialthe combined organic layers were dried (MgSO4)
  9. customevaporated
  10. customto provide 30 g of crude product as an oil
  11. customPurification of the material by HPLC (dichoromethane-hexane; 2:5)

Sources & evidence

ORD record
ord-e0666a73a80e4f5aa807cff2019c93d9
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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