Lithium Hydroxide → 2-[3-(4-Methoxycarbonylmethyl-phenylethynyl)-phenyl]-2-methyl-propionic acid

HRID 2377459Notes

Reaction equation

HRID 2377459 reaction equation
C([O:3][C:4](=[O:27])[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:18][CH:17]=2)[CH:9]=1)([CH3:7])[CH3:6])C.[OH-].[Li+]>C(O)C.O1CCCC1>[CH3:26][O:25][C:23]([CH2:22][C:19]1[CH:18]=[CH:17][C:16]([C:15]#[C:14][C:10]2[CH:9]=[C:8]([C:5]([CH3:7])([CH3:6])[C:4]([OH:27])=[O:3])[CH:13]=[CH:12][CH:11]=2)=[CH:21][CH:20]=1)=[O:24]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 690691802-[3-(4-Methoxycarbonylmethyl-phenylethynyl)-phenyl]-2-methyl-propionic acid ethyl ester2×

Product 1

HCID 211071202-[3-(4-Methoxycarbonylmethyl-phenylethynyl)-phenyl]-2-methyl-propionic acidYield 99.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[3-(4-methoxycarbonylmethyl-phenylethynyl)-phenyl]-2-methyl-propionic acid ethyl ester (Intermediate 133, 0.12 g, 0.33 mmol) in ethanol (2 mL) and tetrahydrofuran (2 mL) was treated with 2M lithium hydroxide (1 mL, 2 mmol) and the resulting reaction mixture was stirred at ambient temperature for 1 h. The volatiles were evaporated in vacuo to a residue that was neutralized with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was washed with water and brine, and dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product as an oil (0.11 g, 95%).

Workup

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo to a residue that
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-efe75c53c19d43bfa47ae5af919487a1
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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