Hydrochloric Acid → HCID 19046358, compound

HRID 2396647Notes

Reaction equation

HRID 2396647 reaction equation
[CH3:1][O:2][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(C2C=CC(C)=CC=2)(=O)=O)[C:4]=1[CH2:25][C:26]1[CH2:30][CH2:29][CH:28]([CH2:31][C:32]([OH:34])=[O:33])[C:27]=1[CH3:35].O.[OH-].[Li+].Cl>CO.O.C(OCC)(=O)C>[OH:14][C:5]1[C:4]([CH2:25][C:26]2[CH2:30][CH2:29][CH:28]([CH2:31][C:32]([OH:34])=[O:33])[C:27]=2[CH3:35])=[C:3]([O:2][CH3:1])[C:11]([CH3:12])=[C:10]2[C:6]=1[C:7](=[O:13])[O:8][CH2:9]2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 18987779HCID 18987779, compound

Product 1

HCID 19046358HCID 19046358, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 3-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranylmethyl)-2-methylcyclopent-2-en-1-ylacetic acid obtained in Example ZC-1G was dissolved in a mixture of methanol (8 mL) and water (2 mL) and treated with lithium hydroxide monohydrate (0.15 g). After 4 hours, the reaction was diluted with ethyl acetate and made acidic with 5% hydrochloric acid. After two extractions with ethyl acetate, the product was washed out of the combined organic layers with 2M NaOH. Acidification of the basic layers with 5% hydrochloric acid and extraction of the product into ethyl acetate was followed by drying the organic layer with magnesium sulfate. Filtration and solvent removal was followed by two flash chromatographies (hexanes/ethyl acetate, 4/1 with 1% HOAc; then methylene chloride/methanol 25/1) to provide 3-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranylmethyl)-2-methylcyclopent-2-en-1-ylacetic acid (0.010 g) m.p. 153°-159° C.

Workup

  1. extractionAfter two extractions with ethyl acetate
  2. washthe product was washed out of the combined organic layers with 2M NaOH
  3. extractionAcidification of the basic layers with 5% hydrochloric acid and extraction of the product into ethyl acetate
  4. dry with materialby drying the organic layer with magnesium sulfate
  5. filtrationFiltration and solvent removal

Sources & evidence

ORD record
ord-fc2fbfa44e2f406ebf3d141021c3e606
Source dataset
uspto-grants-1996_02
Patent number
US05493030

Reaction notes

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