Ethane → 1-(1-Acetyloxycyclohexyl)-3-benzyloxy-1-propyne

HRID 867108Notes

Reaction equation

HRID 867108 reaction equation
[CH2:1]([O:8][CH2:9][C:10]#[CH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Mg]Br)C.CC.[C:18]1(=[O:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>CCOCC.Cl.O1CCCC1>[C:25]([O:24][C:18]1([C:11]#[C:10][CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)(=[O:27])[CH3:26]

Participants

9

Reactant 5

HCID 6324EthaneHCID 7918Acetic AnhydrideHCID 7967CyclohexanoneHCID 6917484((Prop-2-yn-1-yloxy)methyl)benzeneHCID 178418443HCID 178418443, compound

Product 1

HCID 203173761-(1-Acetyloxycyclohexyl)-3-benzyloxy-1-propyne

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-benzyloxy-1-propyne (1 molar equivalent) in dry ether is added dropwise to a stirred solution of ethylmagnesium bromide (1 molar equivalent) in ether at ambient temperature under a nitrogen atmosphere. Upon completing the addition, the reaction mixture is stirred at ambient temperature until gas evolution (ethane generation) ceases, then is cooled to 0° to 5° C. and treated with cyclohexanone (1 molar equivalent) added dropwise at such a rate as to prevent the reaction mixture from attaining room temperature. After completing the addition, the reaction mixture is allowed to warm to room temperature, then is heated at reflux for 1 hour. In vacuo evaporation of the reaction mixture at 40° C. provides a gelatinous residue which is treated with anhydrous tetrahydrofuran and acetic anhydride (1 molar equivalent) and then heated at reflux under a nitrogen atmosphere for 1/2 hour. After cooling to 0° to 5° C., the reaction mixture is slowly diluted with cold 2 N hydrochloric acid, stirred at 0° to 5° C. for 15 minutes and allowed to warm to room temperature. The resulting turbid reaction mixture is extracted several times with ether. The combined organic extract is washed with water (until washings are neutral to Litmus paper) and saturated aqueous brine, dried over sodium sulfate, and filtered. Evaporation (in vacuo at 40° C.) of the filtrate provides the title compound as an essentially colorless oil.

Workup

  1. additionthe addition
  2. temperatureis cooled to 0° to 5° C.
  3. additionadded dropwise at such a rate as
  4. customfrom attaining room temperature
  5. additionthe addition
  6. temperatureis heated
  7. temperatureat reflux for 1 hour
  8. customIn vacuo evaporation of the reaction mixture at 40° C.
  9. customprovides a gelatinous residue which
  10. temperatureheated
  11. temperatureat reflux under a nitrogen atmosphere for 1/2 hour
  12. temperatureAfter cooling to 0° to 5° C.
  13. temperatureto warm to room temperature
  14. customThe resulting turbid reaction mixture
  15. extractionis extracted several times with ether
  16. extractionThe combined organic extract
  17. washis washed with water (until washings are neutral to Litmus paper) and saturated aqueous brine
  18. dry with materialdried over sodium sulfate
  19. filtrationfiltered
  20. customEvaporation (in vacuo at 40° C.) of the filtrate

Sources & evidence

ORD record
ord-de4d70077efd4a668326ae7c1042b116
Source dataset
uspto-grants-1978_07
Patent number
US04102888

Reaction notes

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