Water → 3-(Bis(benzyloxy)phosphoryl)propanoic acid

HRID 1091464Notes

Reaction equation

HRID 1091464 reaction equation
[CH2:1]([O:8][P:9]([O-:18])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:23]CC)(=[O:22])[CH:20]=[CH2:21].C([O-])([O-])=O.[K+].[K+].O>C1COCC1>[CH2:11]([O:10][P:9]([CH2:21][CH2:20][C:19]([OH:23])=[O:22])([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8821Ethyl AcrylateHCID 11430Potassium CarbonateHCID 21904359Dibenzylphosphite

Product 1

HCID 462238443-(Bis(benzyloxy)phosphoryl)propanoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of dibenzylphosphite (2.6 mmol) in 10 mL of THF was added ethyl acrylate (3.0 mmol), K2CO3 (16 mmol), and 0.3 mL of (Bn4NH)2SO4 50% w/w. The reaction mixture was stirred at 45° C. overnight. Water was added. The aqueous layer was extracted with ethyl acetate. Organic layer was collected and dried with MgSO4. Solvent was removed to afford a clear oil 3-bis(benzyloxy)phosphorylpropanoic acid in 90% yield. 1H-NMR (CDCl3, 400 MHz): 7.33 (m, 10H), 4.90-5.10 (m, 4H), 3.61 (s, 3H), 2.50-2.60 (m, 2H), 2.00-2.15 (m, 2H).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. customOrganic layer was collected
  3. dry with materialdried with MgSO4
  4. customSolvent was removed

Sources & evidence

ORD record
ord-48eaba8f506d46b4b6aeea13ce689fba
Source dataset
uspto-grants-2012_03
Patent number
US08129382B2

Reaction notes

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