Lithium hydroxide, monohydrate → HCID 67265201, compound

HRID 1685810Notes

Reaction equation

HRID 1685810 reaction equation
[F:1][C:2]1([F:21])[CH2:6][CH2:5][S:4][C:3]1=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:20])[C:15]([O:17]CC)=[O:16])=[CH:10][CH:9]=1.O.[OH-].[Li+]>C(O)C.O>[F:21][C:2]1([F:1])[CH2:6][CH2:5][S:4][C:3]1=[CH:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]([CH3:20])[C:15]([OH:17])=[O:16])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67265449HCID 67265449, compound

Product 1

HCID 67265201HCID 67265201, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Ethyl 2-[4-(3,3-difluorothiolan-2-ylidenemethyl)phenyl]propionate (43 mg) obtained in Example 24 was dissolved in a solution of ethanol/water (1/1, 1.0 ml), and to the solution was added lithium hydroxide monohydrate (20 mg), and the reaction mixture was stirred at room temperature for 16.5 hours. After completion of the reaction, to the reaction mixture was added 2.0 M aqueous hydrochloric acid, phase separation was performed with ethyl acetate, and the organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=10/1) to give the title compound (33.3 mg, 85.1%).

Workup

  1. customAfter completion of the reaction
  2. additionto the reaction mixture was added
  3. custom2.0 M aqueous hydrochloric acid, phase separation
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-1e3831d16b4d47e0855ddffe38697681
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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