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

HRID 2048999Notes

Reaction equation

HRID 2048999 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-].[CH2:20](I)[CH3:21]>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][CH2:20][CH3:21])=[CH:11][CH:10]=3)([CH2:6]2)[CH2:4]1)=[O:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 19660Carbonate IonHCID 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 potassim 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-5e9daad682a24c16a649a652f5ae6cf0
Source dataset
uspto-grants-1980_04
Patent number
US04196120

Reaction notes

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