Tetrahydrofuran → 2'-Ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylic acid

HRID 400763Notes

Reaction equation

HRID 400763 reaction equation
C([C:3]1([CH2:19][O:20][CH3:21])[CH2:8][C:7]([C:9]([O:11]C)=[O:10])=[CH:6][CH:5]=[C:4]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C.O.[OH-].[Li+].[CH2:25]1COC[CH2:26]1>O>[CH2:25]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:4]1[CH:5]=[CH:6][C:7]([C:9]([OH:11])=[O:10])=[CH:8][C:3]=1[CH2:19][O:20][CH3:21])[CH3:26]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 67401037Methyl 2-ethyl-2-(methoxymethyl)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 594958092'-Ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylic acidYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 2-ethyl-2-(methoxymethyl)-1,1′-biphenyl-4-carboxylate (12 g, 0.0422 mol) in THF (150 mL) and water (30 mL), was added lithium hydroxide monohydrate (5.31 g, 0.127 mol) in portions. After 12 h at RT, the reaction mixture was concentrated and the aqueous phase was acidified using conc. HCl and extracted with EtOAc. Then the organic layers were washed with water and brine solution. The solvents were dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as a white solid (9 g, 80%). 1H NMR (DMSO-d6, 300 MHz) δ 12.9 (1H, bs), 8.08 (1H, s), 7.88-7.90 (1H, m), 7.34-7.35 (2H, m), 7.21-7.25 (2H, m), 7.03-7.05 (1H, m), 4.04-4.13 (2H, m), 3.16-3.18 (3H, s), 2.29-2.38 (1H, m), 2.19-2.24 (1H, m), 0.92-0.95 (3H, m). LC/MS (Method A): 269.0 (M−H)−. HPLC (Method B) Rt 5.06 min (Purity: 97.4%).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. extractionextracted with EtOAc
  3. washThen the organic layers were washed with water and brine solution
  4. dry with materialThe solvents were dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-018d230ea6414f9db9009f67dcb23bcd
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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