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

HRID 1413574Notes

Reaction equation

HRID 1413574 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. Tbe reaction is quenched with a mixture of hexane and ice. The aqueous phase is separated and extracted with additional hexane. The combined hexane extracts is washed successively with water and brine. The solution is dried over magnesium sulfate and concentrated. The residue is chromatographed on a silica gel column and is eluted with tolulene to provide the product as an oil.

Workup

  1. additionAfter the addition
  2. customTbe reaction
  3. customis quenched with a mixture of hexane and ice
  4. customThe aqueous phase is separated
  5. extractionextracted with additional hexane
  6. washThe combined hexane extracts is washed successively with water and brine
  7. dry with materialThe solution is dried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue is chromatographed on a silica gel column
  10. washis eluted with tolulene

Sources & evidence

ORD record
ord-9dd63f5884b44e9280b8ede1ad804e75
Source dataset
uspto-grants-1981_02
Patent number
US04250325

Reaction notes

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