Sodium Hydroxide → HCID 178468121, compound

HRID 1013468Notes

Reaction equation

HRID 1013468 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([O:14][CH2:15][CH3:16])([CH3:13])[PH2:11]=[O:12])=[CH:6][CH:5]=1.[OH-].[Na+]>C1COCC1.CO.O>[CH2:15]([O:14][C:10]([CH3:13])([PH2:11]=[O:12])[C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:17])=[O:2])=[CH:5][CH:6]=1)[CH3:16]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 178468122HCID 178468122, compound

Product 1

HCID 178468121HCID 178468121, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(ethoxy-methyl-phosphinoylmethyl)-benzoic acid methyl ester (660 mg, 2.58 mmol) in THF (5 mL) and MeOH (3 mL) was added 1N NaOH (2.58 mL, 2.58 mmol), and the mixture was stirred for 18 h. The mixture was diluted with H2O and washed with EtOAc. The aqueous layer was acidified with 1 N HCl, saturated with NaCl and extracted with a mixture of CHCl3 and MeOH, dried (MgSO4), and filtered. The solvent was evaporated under reduced pressure and the material was used without further purification. 1H NMR (CDCl3, 600 MHz) δ 7.98 (d, J=7.9 Hz, 2H), 7.34 (dd, J=7.9, 2.0 Hz, 2H), 4.12-4.03 (m, 2H), 3.26 (dd, J=25.2, 14.2 Hz, 1H), 3.23 (dd, J=25.2, 14.2 Hz, 1H), 1.44 (d, J=13.8 Hz, 3H), 1.30 (t, J=7.0 Hz, 3H). MS: cal'd 243 (MH+), exp 243 (MH+).

Workup

  1. washwashed with EtOAc
  2. extractionextracted with a mixture of CHCl3 and MeOH
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customthe material was used without further purification

Sources & evidence

ORD record
ord-166852348d4048b4a4a9271eea3b6687
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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