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

HRID 1525228Notes

Reaction equation

HRID 1525228 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:20])[C:16]([O:18]C)=[O:17])=[CH:11][CH:10]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].O[Li].O>CO.O>[CH2:7]([O:6][P:4]([C:9]1[CH:10]=[CH:11][C:12]([CH:15]([CH3:20])[C:16]([OH:18])=[O:17])=[CH:13][CH:14]=1)([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 89464879Methyl 2-(4-(diethoxyphosphoryl)phenyl)propanoate

Product 1

HCID 177643522-(4-(Diethoxyphosphoryl)phenyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of compound 7-f (100 mg, 0.33 mmol) in methanol (2 mL) and water (2 mL) was treated with LiOH—H2O (14 mg, 0.33 mmol), and the resulting reaction solution was stirred at room temperature overnight. The resulting mixture was concentrated and extracted by EA. The aqueous layers was added HCl (1 M) until pH 1˜2. The mixture was extracted by EA. Combined organic layers was washed by brine, dried over Na2SO4 and concentrated to afford the title compound, 7-g, as oil (35 mg, 37%). 1H NMR (300 MHz, CDCl3) δ1.30-1.34 (m, 6H), 1.52 (d, J=7.2 Hz, 3H), 3.79 (q, J=7.2 Hz, 1H), 4.07-4.17 (m, 4H), 7.39-7.43 (m, 2H), 7.71-7.78 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-805f70b578b24a41a82a019477d822f7
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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