Lithium Hydroxide → 6-(1,3-Dihydro-6-hydroxy-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoic acid

HRID 260112Notes

Reaction equation

HRID 260112 reaction equation
[CH3:1][C:2]1[C:3](C=C)=[C:4]([CH2:23]/[CH:24]=[C:25](\[CH3:32])/[CH2:26][CH2:27][C:28]([O:30]C)=[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].[OH-].[Li+].S([O-])(O)(=O)=[O:38].[Na+]>CO.O>[OH:38][C:3]1[C:2]([CH3:1])=[C:10]2[C:6]([C:7](=[O:11])[O:8][CH2:9]2)=[C:5]([O:12][S:13]([C:16]2[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=2)(=[O:14])=[O:15])[C:4]=1[CH2:23][CH:24]=[C:25]([CH3:32])[CH2:26][CH2:27][C:28]([OH:30])=[O:29]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 516919Sodium BisulfateHCID 10672508methyl (E) 6-(1,3-dihydro-7-methyl-3-oxo-4-p-toluenesulfonyloxy-6-vinylisobenzofuran-5-yl)-4-methyl-4-hexenoate

Product 1

HCID 536610776-(1,3-Dihydro-6-hydroxy-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl (E) 6-(1,3-dihydro-7-methyl-3-oxo-4-p-toluenesulfonyloxy-6-vinyl isobenzofuran-5-yl)-4-methyl-4-hexenoate (0.37 g) and lithium hydroxide (0.4 g) in methanol (6 ml) and water (6 ml) was heated at 62° C. for 15 hours. The reaction was acidified with aqueous sodium hydrogen sulfate and extracted with ethyl acetate. The extract was dried and evaporated and the residue chromatographed on silica gel, eluting with ethyl acetate/hexane/acetic acid to give (E) 6-(1,3-dihydro-4-hydroxy-7-methyl-3-oxo-6-vinylisobenzofuran-5-yl)-4-methyl-4-hexenoic acid, m.p. 148° 149° C. (tert-butylmethyl ether/hexane).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extract was dried
  3. customevaporated
  4. customthe residue chromatographed on silica gel
  5. washeluting with ethyl acetate/hexane/acetic acid

Sources & evidence

ORD record
ord-40c22849e91f4bbb887f02b96e2bd757
Source dataset
uspto-grants-1996_06
Patent number
US05525602

Reaction notes

Loading…