4-Oxo-1-iodo-trans-1-octene → 4-Hydroxy-4-vinyl-1-iodo-trans-1-octene

HRID 262910Notes

Reaction equation

HRID 262910 reaction equation
[CH:1]([Mg]Cl)=[CH2:2].[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]([CH:1]=[CH2:2])([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 178461836HCID 178461836, compound

Product 1

HCID 128512814-Hydroxy-4-vinyl-1-iodo-trans-1-octene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 7.8 ml of vinyl magnesium chloride (2.3M in tetrahydrofuran), at -25° C. is added a solution of 3.55 g of 4-oxo-1-iodo-trans-1-octene in 20 ml of tetrahydrofuran during 15 minutes. After the addition, the solution is stirred at -20° C. 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 concentated. The residue is subjected to dry column chromatography on silica gel with benzene as developing solvent to give a liquid, pmr specturm (CDCl3): 5.2 (m, terminal CH2), 5.83 (q, CH=CH2), 6.13 (d, ICH=), and 6.52 (m, ICM=CH).

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. dry with materialto dry column chromatography on silica gel with benzene
  8. customto give a liquid, pmr specturm (CDCl3)

Sources & evidence

ORD record
ord-b428f2734dd5455f993eaf440b888390
Source dataset
uspto-grants-1979_05
Patent number
US04154954

Reaction notes

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