Diiodomethane → HCID 22235737, compound

HRID 1441045Notes

Reaction equation

HRID 1441045 reaction equation
[CH2:1]([Zn]CC)C.[CH3:6][C:7](=[CH2:15])[CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].ICI.[Cl-].[NH4+]>CCCCCC>[CH3:15][C:7]1([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:1][CH2:6]1

Participants

6

Reactant 4

HCID 6346DiiodomethaneHCID 25517Ammonium ChlorideHCID 3416433Ethyl 4-methyl-4-pentenoateHCID 178418750HCID 178418750, compound

Product 1

HCID 22235737HCID 22235737, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Diethylzinc (40 ml. 1.1M solution in toluene) was added dropwise to a solution of ethyl 4-methylpent-4-enoate (1.25 g.) in dry hexane (100 ml.) at -20° under nitrogen After stirring for 10 minutes diiodomethane (23.6 g.) was added dropwise and the mixture maintained at -20° for 6 hours. The mixture was allowed to warm to room temperature, aqueous ammonium chloride solution (60 ml.) added and the two layers separated. The aqueous layer was extracted with diethyl ether (3×50 ml.) and the combined organic extracts washed with sodium thiosulphate solution (50 ml.) and water (50 ml.). The extracts were dried over anhydrous magnesium sulphate and evaporated in vacuo. Chromatography on silica, eluting with diethyl ether/hexane mixtures, gave ethyl 3-(1-methylcyclopropyl)propanoate as a colourless oil (1.21 g.).

Workup

  1. additionwas added dropwise
  2. temperaturethe mixture maintained at -20° for 6 hours
  3. customthe two layers separated
  4. extractionThe aqueous layer was extracted with diethyl ether (3×50 ml.)
  5. washthe combined organic extracts washed with sodium thiosulphate solution (50 ml.) and water (50 ml.)
  6. dry with materialThe extracts were dried over anhydrous magnesium sulphate
  7. customevaporated in vacuo
  8. washChromatography on silica, eluting with diethyl ether/hexane mixtures

Sources & evidence

ORD record
ord-23e4ee87cb1a4da8ad6e13941bc19131
Source dataset
uspto-grants-1996_03
Patent number
US05502073

Reaction notes

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