Lithium hydroxide, monohydrate → HCID 67191559, compound

HRID 546152Notes

Reaction equation

HRID 546152 reaction equation
C[O:2][C:3](=[O:20])[CH:4]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.O.[OH-].[Li+]>O1CCCC1.C(O)C.O.S([O-])(O)(=O)=O.[K+]>[Cl:19][C:14]1[CH:13]=[C:12]([CH:4]([CH2:5][CH:6]2[CH2:7][CH2:8][O:9][CH2:10][CH2:11]2)[C:3]([OH:20])=[O:2])[CH:17]=[CH:16][C:15]=1[Cl:18]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67188333HCID 67188333, compound

Product 1

HCID 67191559HCID 67191559, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 516920Potassium bisulfateSolventHCID 18504229Ethanol tetrahydrofuran waterSolvent

Conditions

Temperature
25 °C

Procedure

2-(3,4-Dichloro-phenyl)-3-(tetrahydro-pyran-4-yl)-propionic acid methyl ester (2.26 g, 7.12 mmol) was dissolved in tetrahydrofuran:ethanol:water (6:3:2) reaction (100 mL) and treated with lithium hydroxide monohydrate (1.50 g, 35.6 mmol) at 25° C. It was stirred at 25° C. for 2 h. The reaction was then diluted with a 1 M aqueous solution of potassium hydrogen sulfate (200 mL) and then extracted with ethyl acetate (1×300 mL), the organic layers combined and dried over sodium sulfate, filtered and concentrated in vacuo with silica gel (4 g) and purified by Biotage Flash Chromatography (40M column, Silica gel, 10% methanol/ethyl acetate) to afford 2-(3,4-dichloro-phenyl)-3-(tetrahydro-pyran-4-yl)-propionic acid (2.00 g, 93%) as an off white solid.

Workup

  1. customreaction (100 mL)
  2. extractionextracted with ethyl acetate (1×300 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo with silica gel (4 g)
  6. custompurified by Biotage Flash Chromatography (40M column, Silica gel, 10% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-a85714f63e4e487a94d7a1db9ae60b45
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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