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

HRID 1757206Notes

Reaction equation

HRID 1757206 reaction equation
C([C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:4]=1[CH2:25]/[CH:26]=[C:27](\[CH3:34])/[CH2:28][CH2:29][C:30]([O:32]C)=[O:31])C.[OH-:35].[Li+]>CO>[OH:35][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:16])=[O:17])[C:4]=1[CH2:25][CH:26]=[C:27]([CH3:34])[CH2:28][CH2:29][C:30]([OH:32])=[O:31]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10696303methyl (E) 6-(1,3-dihydro-6-ethyl-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-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 1

HCID 887MethanolSolvent

Procedure

A solution of methyl (E) 6-(1,3-dihydro-6-ethyl-7-methyl-3-oxo-4-p-toluenesulfonyloxylisobenzofuran-5-yl)-4-methyl-4-hexenoate (3.16 g) and lithium hydroxide (1.2 g) in 1:1 aqueous methanol (40 ml) was heated at 62° C. for 18 hours. The solution was acidified and extracted with ethyl acetate. The extract was dried and evaporated and the residue chromatographed on silica gel, eluting wth ethyl acetate/hexane/acetic acid to afford (E) 6-(1,3-dihydro-6-ethyl-4-hydroxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic acid, m.p. 141°-142° C. (t-butylmethylether).

Workup

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

Sources & evidence

ORD record
ord-17266ebfde124ec3ba6575b850761852
Source dataset
uspto-grants-1995_08
Patent number
US05444072

Reaction notes

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