Iodine → 1-Iodo-4-propadienyl-4-trimethylsilyloxy-trans-octene

HRID 224701

Reaction equation

HRID 224701 reaction equation
[CH:1]([C:4]([O:12][Si:13]([CH3:16])([CH3:15])[CH3:14])([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:5][C:6]#[CH:7])=[C:2]=[CH2:3].CC(C)C(BC(C(C)C)C)C.C([N+]([O-])(CC)CC)C.[I:36]I>O1CCCC1.C(COC)OC>[I:36]/[CH:3]=[CH:2]/[CH2:1][C:4]([CH:5]=[C:6]=[CH2:7])([O:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

7

Reactant 4

HCID 807IodineHCID 123168Ethanamine, N,N-diethyl-, N-oxideHCID 192733Bis(1,2-dimethylpropyl)boraneHCID 130391894-Propadienyl-4-trimethylsilyloxy-1-octyne

Product 1

HCID 130391901-Iodo-4-propadienyl-4-trimethylsilyloxy-trans-octene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 2.36 g. (10 mmol.) of 4-propadienyl-4-trimethylsilyloxy-1-octyne in 5 ml. of glyme is added a solution of 11 mmol. of bis-(3-methyl-2-butyl)borane in 15 ml. of glyme at 0° C. The mixture is stirred at 25° C. for 90 minutes, cooled to 0° C., and treated portionwise with 3.0 g. of triethylamine oxide. The stirred mixture is maintained at 25°-30° C. for 45 minutes, diluted with 20 ml. of tetrahydrofuran and poured into 100 ml. of ice-cold 15% sodium hydroxide solution, followed immediately with a solution of 8.0 g. of iodine in 20 ml. of tetrahydrofuran. The mixture is stirred at ambient temperature for 30 minutes and then extracted with ether. The extract is washed successively with water, sodium thiosulfate solution and brine; dried over magnesium sulfate; and filtered. The residue obtained after solvent evaporation is subjected to chromatography on silica gel with heptane solvent to afford the title compound as a liquid.

Workup

  1. customat 0° C
  2. temperaturecooled to 0° C.
  3. additiontreated portionwise with 3.0 g
  4. temperatureThe stirred mixture is maintained at 25°-30° C. for 45 minutes
  5. additiondiluted with 20 ml
  6. stirringThe mixture is stirred at ambient temperature for 30 minutes
  7. extractionextracted with ether
  8. washThe extract is washed successively with water, sodium thiosulfate solution and brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationand filtered
  11. customThe residue obtained
  12. customafter solvent evaporation

Sources & evidence

ORD record
ord-6175d75416494992b00737b2d388915a
Source dataset
uspto-grants-1980_11
Patent number
US04233453

Linked notes

Loading…