Lithium Hydroxide → 3-(3-(((2-Methyl-3'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)propanoic acid

HRID 1662312Notes

Reaction equation

HRID 1662312 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH2:16][CH2:17][C:18]([O:20]C)=[O:19])[CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1.[Li+].[OH-]>C1COCC1.CO>[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57705995Methyl 3-(3-(((2-methyl-3'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)propanoate

Product 1

HCID 252612983-(3-(((2-Methyl-3'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)propanoic acidYield 83.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 1.4 (0.0532 g, 0.136 mmol) in THF/MeOH (2/1) (1.5 mL) was added LiOH (0.50 mL, 0.500 mmol). The resulting mixture was stirred overnight at 23° C., quenched with excess 1N HCl, and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The crude residue was purified by combiflash (0 to 40% EtOAc/hexane) to afford 1 (0.0426 g, 83.1% yield). MS ESI (neg.) m/e: 375.1 (M−H)+. 1H NMR (400 MHz, CDCl3) δ ppm 7.32-7.39 (3H, m), 7.24-7.31 (2H, m), 6.85-6.95 (6H, m), 5.08 (2H, s), 3.87 (3H, s), 2.99 (2H, t, J=7.8 Hz), 2.73 (2H, t, J=7.8 Hz), 2.34 (3H, s).

Workup

  1. customquenched with excess 1N HCl
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude residue was purified by combiflash (0 to 40% EtOAc/hexane)

Sources & evidence

ORD record
ord-ecf45693525448578355ea2f8cf9bed3
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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