Lithium hydroxide, monohydrate → 2-(4-(Diethoxyphosphoryl)phenyl)-2-phenylacetic acid

HRID 1525244Notes

Reaction equation

HRID 1525244 reaction equation
C[O:2][C:3]([CH:5]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:6]1[CH:11]=[CH:10][C:9]([P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])=[CH:8][CH:7]=1)=[O:4].O[Li].O>CO.O>[CH2:17]([O:16][P:12]([C:9]1[CH:10]=[CH:11][C:6]([CH:5]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:3]([OH:4])=[O:2])=[CH:7][CH:8]=1)([O:13][CH2:14][CH3:15])=[O:19])[CH3:18]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 89462076Diethyl 4-((methoxycarbonyl)(phenyl)methyl)phenylphosphonate2×

Product 1

HCID 894624812-(4-(Diethoxyphosphoryl)phenyl)-2-phenylacetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of Diethyl 4-((methoxycarbonyl)(phenyl)methyl)phenylphosphonate, 14-e, (1.7 g, 5.0 mmol) and LiOH.H2O (0.3 g, 7 mmol) in methanol (10 mL) and H2O (10 mL) was stirred overnight. The resulting mixture was concentrated and extracted by EA. The aqueous layers were added HCl (1 M) until pH 1˜2. The mixture was extracted by EA. Combined organic layers were washed with brine, dried over Na2SO4 and concentrated to afford the title compound, 14-f, as colorless oil (1.18 g, 72%). 1H NMR (300 MHz, CDCl3) δ1.22-1.31 (m, 6H), 4.03-4.14 (m, 4H), 5.05 (s, 1H), 7.25-7.31 (m, 5H), 7.38-7.42 (m, 2H), 7.68-7.75 (m, 2H); LC-MS: (M+H)+ 349.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. extractionextracted by EA
  3. additionThe aqueous layers were added HCl (1 M) until pH 1˜2
  4. extractionThe mixture was extracted by EA
  5. washCombined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-003be09a271e478095fe22db822dc4bf
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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