4-Oxo-1-iodo-trans-1-octene → 4-Hydroxy-4-(1-propynyl)-1-iodo-trans-1-octene

HRID 1449359Notes

Reaction equation

HRID 1449359 reaction equation
[C:1]([Li])#[C:2][CH3:3].[O:5]=[C:6]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7]/[CH:8]=[CH:9]/[I:10]>O1CCCC1>[OH:5][C:6]([C:1]#[C:2][CH3:3])([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7]/[CH:8]=[CH:9]/[I:10]

Participants

4

Reactant 2

HCID 128512804-Oxo-1-iodo-trans-1-octeneHCID 178506788HCID 178506788, compound

Product 1

HCID 205650814-Hydroxy-4-(1-propynyl)-1-iodo-trans-1-octene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of propynyllithium at -25° is added a solution of 4-oxo-1-iodo-trans-1-octene in tetrahydrofuran. After the addition, the solution is stirred at -20° to -15° C. for 30 minutes. The reaction is quenched with a mixture of hexane and ice. The aqueous phase is separated and extracted with additional hexane. The combined hexane extracts are washed successively with water and brine. The solution is dried over magnesium sulfate and concentrated. The residue is subjected to column chromatography on silica gel with toluene to provide the product as an oil.

Workup

  1. additionAfter the addition
  2. customThe reaction is quenched with a mixture of hexane and ice
  3. customThe aqueous phase is separated
  4. extractionextracted with additional hexane
  5. washThe combined hexane extracts are washed successively with water and brine
  6. dry with materialThe solution is dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9c9c158dc0f846f98357c6a33b80690d
Source dataset
uspto-grants-1980_02
Patent number
US04190596

Reaction notes

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