Ammonium Chloride → 5-methoxy-1-propyl-1H-indene

HRID 7874

Reaction equation

HRID 7874 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]=[CH:6]2.[Li]C.I[CH2:15][CH2:16][CH3:17].[NH4+].[Cl-]>CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([CH2:15][CH2:16][CH3:17])[CH:7]=[CH:6]2

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 336431-IodopropaneHCID 127219015-Methoxy-1H-indeneHCID 178418348HCID 178418348, compound

Product 1

HCID 219909075-methoxy-1-propyl-1H-indeneYield 108.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 5-methoxy-1H-indene (0.895 g, 6.12 mmol) in anhydrous Et2O (7.5 mL) was treated with 1.4M MeLi in Et2O (4.7 mL, 6.58 mmol) added dropwise over 10 minutes. The resulting hazy solution was stirred at room temperature an additional 15 minutes, then cooled in an ice bath and treated with iodopropane (1.00 mL, 10.3 mmol). The mixture was stirred at ice bath temperature with gradual warming to room temperature. After stirring at room temperature overnight, the mixture was treated with saturated aq. NH4Cl (10 mL) and Et2O (15 mL) and shaken. The organic phase was washed with brine, dried over MgSO4, filtered, and evaporated under vacuum to afford a mixture (1.248 g) of 5-methoxy-1-propyl-1H-indene and 6-methoxy-1-propyl-1H-indene as an oil.

Workup

  1. additionadded dropwise over 10 minutes
  2. temperaturecooled in an ice bath
  3. stirringThe mixture was stirred at ice bath temperature
  4. temperaturewith gradual warming to room temperature
  5. stirringAfter stirring at room temperature overnight
  6. stirringshaken
  7. washThe organic phase was washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated under vacuum

Sources & evidence

ORD record
ord-d0bd1b0c03f844d7a23d87971c34bc62
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Linked notes

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