N-methyl-2-pyrrolidone → methyl (E) 6-(1,3-dihydro-6-(4-methoxybenzyloxymethyl)-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoate

HRID 742354Notes

Reaction equation

HRID 742354 reaction equation
[CH3:1][C:2]1[C:3](OS(C(F)(F)F)(=O)=O)=[C:4]([CH2:23][CH:24]=[C:25]([CH3:31])[CH2:26][CH2:27][C:28]([O-:30])=[O:29])[C:5]([O:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[C:6]2[C:10]=1[CH2:9][O:8][C:7]2=[O:11].[CH3:40]N1CCCC1=O.[CH3:47][O:48][C:49]1[CH:70]=[CH:69][C:52]([CH2:53][O:54][CH2:55][Sn](CCCC)(CCCC)CCCC)=[CH:51][CH:50]=1.[F-].[K+]>C(OCC)(=O)C.O>[CH3:47][O:48][C:49]1[CH:70]=[CH:69][C:52]([CH2:53][O:54][CH2:55][C:3]2[C:2]([CH3:1])=[C:10]3[C:6]([C:7](=[O:11])[O:8][CH2:9]3)=[C:5]([O:12][S:13]([C:16]3[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=3)(=[O:14])=[O:15])[C:4]=2[CH2:23]/[CH:24]=[C:25](\[CH3:31])/[CH2:26][CH2:27][C:28]([O:30][CH3:40])=[O:29])=[CH:51][CH:50]=1

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 522689Potassium FluorideHCID 11166591Tributyl({[(4-methoxyphenyl)methoxy]methyl})stannaneHCID 867498026-(1,3-Dihydro-7-methyl-3-oxo-4-p-toluenesulfonyloxy-6-trifluoromethanesulfonyloxy-isobenzofuran-5-yl)-4-methyl-4-hexenoate

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 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-(1,3-dihydro-7-methyl-3-oxo-4-p-toluenesulfonyloxy-6-trifluoromethanesulfonyloxy-isobenzofuran-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-(4-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-b518e0c4478b40aaa30c9915c6c369dc
Source dataset
uspto-grants-1996_09
Patent number
US05554612

Reaction notes

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