Potassium Carbonate → 2-Methoxy-5-nitro-indan

HRID 1881356Notes

Reaction equation

HRID 1881356 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([OH:13])[CH2:7]2)([O-:3])=[O:2].[C:14]([O-])([O-])=O.[K+].[K+]>>[CH3:14][O:13][CH:8]1[CH2:7][C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:9]1

Participants

3

Reactant 2

HCID 11430Potassium CarbonateHCID 36859272-Hydroxy-5-nitroindane

Product 1

HCID 143168082-Methoxy-5-nitro-indanYield 74%

Procedure

5-nitro-indan-2-ol (1.55 g, 8.65 mmol) and K2CO3 (2.8 g, 20 mmol) was charged into a schlenk flask. The flask was evacuated and back filled with N2. DMF (10 mL) was added and stirred at r.t. for 30 min. MeI (excess, 10 mL) was added and the reaction mixture was stirred at 100° C. overnight. The reaction mixture was allowed to cool to room temperature. Water was added and the reaction mixture was extracted with EtOAc. The combined organic layers were washed with water and brine and dried over Na2SO4. Purification of the concentrated crude product by column chromatography (EtOAc:Hexane=1:9) afforded the title product as a pale yellow oil (520 mg, 74% based on recovered starting material).

Workup

  1. customThe flask was evacuated
  2. additionback filled with N2
  3. additionDMF (10 mL) was added
  4. additionMeI (excess, 10 mL) was added
  5. stirringthe reaction mixture was stirred at 100° C. overnight
  6. temperatureto cool to room temperature
  7. additionWater was added
  8. extractionthe reaction mixture was extracted with EtOAc
  9. washThe combined organic layers were washed with water and brine
  10. dry with materialdried over Na2SO4
  11. customPurification of the
  12. concentrationconcentrated crude product by column chromatography (EtOAc:Hexane=1:9)

Sources & evidence

ORD record
ord-ec36f50090ef4a3cafe769c70aa25c45
Source dataset
uspto-grants-2012_11
Patent number
US08318790B2

Reaction notes

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