Methyl 2-[[5,6-dihydro-4-hydroxy-6-(3-methylbutyl)-2-oxo-6-phenyl-2H-pyran-3-yl]thio]benzoate → 2-[[5,6-Dihydro-4-hydroxy-6-(3-methylbutyl)-2-oxo-6-phenyl-2H-pyran-3-yl]thio]benzoic acid

HRID 357860Notes

Reaction equation

HRID 357860 reaction equation
[OH:1][C:2]1[CH2:7][C:6]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:19])[C:3]=1[S:20][C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=1[C:23]([O:25]C)=[O:24]>[OH-].[Na+]>[OH:1][C:2]1[CH2:7][C:6]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:19])[C:3]=1[S:20][C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=1[C:23]([OH:25])=[O:24]

Participants

3

Reactant 1

HCID 54721562Methyl 2-[[5,6-dihydro-4-hydroxy-6-(3-methylbutyl)-2-oxo-6-phenyl-2H-pyran-3-yl]thio]benzoate

Product 1

HCID 547217162-[[5,6-Dihydro-4-hydroxy-6-(3-methylbutyl)-2-oxo-6-phenyl-2H-pyran-3-yl]thio]benzoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 0.3 mmol of the compound prepared in Example 77 in 15 mL of 1N sodium hydroxide was stirred at room temperature for 3 hours. The solution was washed with ether and then acidified to pH 2.0 with 6N hydrochloric acid. The solution was extracted with ethyl acetate, and the extract was washed with brine, dried over magnesium sulfate, and concentrated to give the title compound (m.p. 99°-101° C.). 1H NMR (DMSO-d6) δ 0.80 (m, 6 H), 0.95 (m, 1 H), 1.15 (m, 1 H), 1.43 (m, 1 H), 1.91 (m, 2 H), 3.4 (2 H+H2O), 6.05 (d, 1 H), 6.85 (bt, 1 H), 7.03 (t, 1 H), 7.42 (m, 5 H), 7.79 (dd, 1 H).

Workup

  1. washThe solution was washed with ether
  2. extractionThe solution was extracted with ethyl acetate
  3. washthe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-079bbb70cc0547b8bd9c911f53300c50
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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