Lithium hydroxide, monohydrate → HCID 22282554, compound

HRID 2085341Notes

Reaction equation

HRID 2085341 reaction equation
O.[OH-].[Li+].[O:4]=[S:5]1(=[O:25])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]([C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=2)[CH2:7][CH2:6]1>O.C1COCC1.CO>[O:4]=[S:5]1(=[O:25])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]([C:15]2[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=2)[CH2:7][CH2:6]1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22282614HCID 22282614, compound

Product 1

HCID 22282554HCID 22282554, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide hydrate (0.195 g, 4.65 mmol) dissolved in water (1 mL) was added to a solution of methyl 4-(1,1-dioxido-3,4-dihydro-2H-1-benzothiopyran-4-yl)benzoate from reaction 33d (0.49 gm, 1.55 mmol) in THF (5 mL) and methanol (1 mL) under nitrogen atmosphere at room temperature. The reaction was stirred over night, concentrated then partitioned between 1 N HCl and ethyl acetate. The organic layer was washed with water, brine, dried over magnesium sulfate and concentrated to give 4-(1,1-dioxido-3,4-dihydro-2H-1-benzothiopyran-4-yl)benzoic acid (0.46 g, 98%) as an solid. MS found: (M−H)+=301.

Workup

  1. concentrationconcentrated
  2. customthen partitioned between 1 N HCl and ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a5c69832003e4cfd82995312ccb7ee3b
Source dataset
uspto-grants-2004_04
Patent number
US06720329B2

Reaction notes

Loading…