Triphenylarsine → methyl (E) 6-(1,3-dihydro-6-(4-methoxybenzyloxymethyl)-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoate

HRID 1735430Notes

Reaction equation

HRID 1735430 reaction equation
[Cl-].[Li+].C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:22][C:23]1[C:24](OS(C(F)(F)F)(=O)=O)=[C:25]([CH2:44]/[CH:45]=[C:46](\[CH3:53])/[CH2:47][CH2:48][C:49]([O:51][CH3:52])=[O:50])[C:26]([O:33][S:34]([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=2)(=[O:36])=[O:35])=[C:27]2[C:31]=1[CH2:30][O:29][C:28]2=[O:32].[CH3:62][O:63][C:64]1[CH:85]=[CH:84][C:67]([CH2:68][O:69][CH2:70][Sn](CCCC)(CCCC)CCCC)=[CH:66][CH:65]=1.[F-].[K+]>C(OCC)(=O)C.O.CN1CCCC1=O>[CH3:62][O:63][C:64]1[CH:85]=[CH:84][C:67]([CH2:68][O:69][CH2:70][C:24]2[C:23]([CH3:22])=[C:31]3[C:27]([C:28](=[O:32])[O:29][CH2:30]3)=[C:26]([O:33][S:34]([C:37]3[CH:38]=[CH:39][C:40]([CH3:43])=[CH:41][CH:42]=3)(=[O:35])=[O:36])[C:25]=2[CH2:44]/[CH:45]=[C:46](\[CH3:53])/[CH2:47][CH2:48][C:49]([O:51][CH3:52])=[O:50])=[CH:66][CH:65]=1

Participants

9

Reactant 5

HCID 11773TriphenylarsineHCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 10555649methyl (E) 6-(1,3-dihydro-7-methyl-3-oxo-4-p-toluenesulfonyloxy-6-trifluoromethanesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoateHCID 11166591Tributyl({[(4-methoxyphenyl)methoxy]methyl})stannane

Product 1

HCID 15840162methyl (E) 6-(1,3-dihydro-6-(4-methoxybenzyloxymethyl)-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of lithium chloride (1.6 g), tris (dibenzylideneacetone)dipalladium (O) chloroform adduct (0.22 g), triphenylarsine (0.53 g), methyl (E) 6-(1,3-dihydro-7-methyl-3-oxo-4-p-toluenesulfonyloxy-6-trifluoromethanesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoate (8.0 g) and N-methylpyrrolidinone (70 ml) is heated to 55° C. p-Methoxybenzyloxymethyltributyltin (7.5 g) is added. After 3 hours the solution is added to water (200 ml), potassium fluoride (5 g) and ethyl acetate (200 ml). The organic solution is dried, filtered through celite and evaporated, and the residue is chromatographed on silica gel, eluting with hexane:ethyl acetate, to afford methyl (E) 6-(1,3-dihydro-6-(p-methoxybenzyloxymethyl)-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoate.

Workup

  1. additionis added
  2. customThe organic solution is dried
  3. filtrationfiltered through celite
  4. customevaporated
  5. customthe residue is chromatographed on silica gel
  6. washeluting with hexane

Sources & evidence

ORD record
ord-8401077f4b4d4c86aa09e4ae3eebbefc
Source dataset
uspto-grants-1996_07
Patent number
US05536747

Reaction notes

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