Iodoethane → 3-Formyl-1-(p-ethoxyphenyl)-3-azabicyclo[3.1.0]hexane

HRID 224295Notes

Reaction equation

HRID 224295 reaction equation
[CH:1]([N:3]1[CH2:8][CH:7]2[C:5]([C:9]3[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=3)([CH2:6]2)[CH2:4]1)=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:22](I)[CH3:23]>C(O)C>[CH:1]([N:3]1[CH2:8][CH:7]2[C:5]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:22][CH3:23])=[CH:11][CH:10]=3)([CH2:6]2)[CH2:4]1)=[O:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 127198763-Formyl-1-(p-hydroxyphenyl)-3-azabicyclo[3.1.0]hexane

Product 1

HCID 127198823-Formyl-1-(p-ethoxyphenyl)-3-azabicyclo[3.1.0]hexaneYield 27.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred mixture of 1.0 g of 3-formyl-1-(p-hydroxyphenyl)-3-azabicyclo[3.1.0]hexane and 0.7 g of potassium carbonate in 25 ml of absolute ethanol is added a solution of 3.2 g of ethyl iodide in 10 ml of absolute ethanol. The mixture is refluxed for 2 hours and then is filtered and evaporated. The residual mixture of crystals and liquid is combined with water and this is extracted with chloroform and the extract is dried over magnesium sulfate and evaporated to give 1.0 g of a colorless, viscous liquid, which crystallizes on standing. Recrystallization from hexane gives 0.31 g of 3-formyl-1-(p-ethoxyphenyl)-3-azabicyclo[3.1.0]hexane as colorless crystals, m.p. 48°-51° C.

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. filtrationis filtered
  3. customevaporated
  4. additionThe residual mixture of crystals and liquid
  5. extractionthis is extracted with chloroform
  6. dry with materialthe extract is dried over magnesium sulfate
  7. customevaporated
  8. customto give 1.0 g of a colorless, viscous liquid, which
  9. customcrystallizes
  10. customRecrystallization from hexane

Sources & evidence

ORD record
ord-23ae7b409e2c4e6d8be34f741f10ee6a
Source dataset
uspto-grants-1980_11
Patent number
US04231935

Reaction notes

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