Lithium Hydroxide → HCID 67488047, compound

HRID 2371252Notes

Reaction equation

HRID 2371252 reaction equation
C[O:2][C:3](=[O:33])[CH:4]([C:23]1[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:8][CH:7]=1.[OH-].[Li+]>C1COCC1.CO.O>[CH2:16]([O:15][CH2:14][CH2:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH:4]([C:23]2[CH:24]=[CH:25][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:27][CH:28]=2)[C:3]([OH:33])=[O:2])=[CH:7][CH:8]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67486802HCID 67486802, compound

Product 1

HCID 67488047HCID 67488047, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To the crude 3-[4-(2-Benzyloxyethoxy)-phenyl]-2-(4-tert-butylphenyl)-propionic acid methyl ester from step d dissolved in 20 mL of THF/MeOH/H2O (3:1:1) was added lithium hydroxide (270 mg, 6.5 mmol) After stirring for 5 hrs at rt, the organic solvents were removed under vacuum and the reaction residue diluted further with water (25 mL). The aqueous mixture was extracted with diethyl ether, made acidic with 1 N HCl and extracted again with ethyl acetate. The ethyl acetate portion was then dried over Na2SO4 and concentrated under vacuum to afford 3-[4-(2-Benzyloxyethoxy)-phenyl]-2-(4-tert-butylphenyl)-propionic acid as a semi-solid mass. (456 mg, 81% over 2 steps)

Workup

  1. customthe organic solvents were removed under vacuum
  2. additionthe reaction residue diluted further with water (25 mL)
  3. extractionThe aqueous mixture was extracted with diethyl ether
  4. extractionextracted again with ethyl acetate
  5. dry with materialThe ethyl acetate portion was then dried over Na2SO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d25f0be0f82844569003f5aa4942167c
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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