Allyl iodide → HCID 15158218, compound

HRID 704694Notes

Reaction equation

HRID 704694 reaction equation
[CH:1]1([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[O:20][CH2:19][CH2:18][O:17]3)=[CH:12][CH:11]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:21][C:22](C)([O-])[CH3:23].[K+].C(I)C=C.OS([O-])(=O)=O.[K+]>CN(C=O)C>[CH:1]1([CH:7]([CH2:23][CH:22]=[CH2:21])[C:8]([C:10]2[CH:11]=[CH:12][C:13]([CH:16]3[O:17][CH2:18][CH2:19][O:20]3)=[CH:14][CH:15]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 11166Allyl iodide2×HCID 516920Potassium bisulfateHCID 15158214HCID 15158214, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15158218HCID 15158218, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of Example J (1.6 g, 0.006 mole) was dissolved in 30 mls of dry DMF at room temperature under a nitrogen atmosphere and potassium t-butoxide (1.4 g) was added. After stirring for 5 minutes, 1 g of allyl iodide was added and the reaction was warmed to +50° C. for 1 hour. Another half equivalent of allyl iodide was added and the stirring was continued for 2 hours at +50° C. After cooling to room temperature the mixture was poured into 50 mls of 0.5N KHSO4 and extracted with ethyl acetate. After drying the organic layer over Na2SO4, the solvent was removed and the residue was chromatographed on silica gel using 10% ethyl acetate/hexane to give 1 g of the title compound (54% yield).

Workup

  1. temperaturethe reaction was warmed to +50° C. for 1 hour
  2. waitthe stirring was continued for 2 hours at +50° C
  3. extractionextracted with ethyl acetate
  4. dry with materialAfter drying the organic layer over Na2SO4
  5. customthe solvent was removed
  6. customthe residue was chromatographed on silica gel using 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-44c833bdf1fc4ee2a55b3c16d09ff92b
Source dataset
uspto-grants-1991_01
Patent number
US04988707

Reaction notes

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