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

HRID 742355Notes

Reaction equation

HRID 742355 reaction equation
COC1C=CC(C[O:8][CH2:9][C:10]2[C:18]([CH3:19])=[C:17]3[C:13]([C:14](=[O:20])[O:15][CH2:16]3)=[C:12]([O:21][S:22]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[C:11]=2[CH2:32]/[CH:33]=[C:34](\[CH3:41])/[CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=CC=1>FC(F)(F)C(O)=O>[OH:8][CH2:9][C:10]1[C:18]([CH3:19])=[C:17]2[C:13]([C:14](=[O:20])[O:15][CH2:16]2)=[C:12]([O:21][S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[C:11]=1[CH2:32]/[CH:33]=[C:34](\[CH3:41])/[CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38]

Participants

3

Reactant 1

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

Product 1

HCID 86748922methyl (E) 6-(1,3-dihydro-6-hydroxymethyl-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoate

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Methyl (E) 6-(1,3-dihydro-6-(4-methoxybenzyloxymethyl)-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoate (0.5 g) is dissolved in trifluoroacetic acid (10 ml) at 0° C. After 30 minutes the solvent is removed under vacuum and the residue is chromatographed on silica gel, eluting with hexane: ethyl acetate, to afford methyl (E) 6-(1,3-dihydro-6-hydroxymethyl-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoate.

Workup

  1. customAfter 30 minutes the solvent is removed under vacuum
  2. customthe residue is chromatographed on silica gel
  3. washeluting with hexane

Sources & evidence

ORD record
ord-574c959dd7464b25b5e586ebe0ff211c
Source dataset
uspto-grants-1996_09
Patent number
US05554612

Reaction notes

Loading…