Potassium Hydroxide → 3-(2-Hydroxy-5-(Ethoxy(diethylphosphonomethyl)phosphinoyl)phenyl)-3-methylbutanoic acid

HRID 39276Notes

Reaction equation

HRID 39276 reaction equation
[CH2:1]([O:3][P:4]([CH2:19][P:20]([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[O:21])([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11](=[O:16])[CH2:10][C:9]2([CH3:18])[CH3:17])=[O:5])[CH3:2].[OH-:28].[K+]>CO>[OH:12][C:13]1[CH:14]=[CH:15][C:6]([P:4]([O:3][CH2:1][CH3:2])([CH2:19][P:20]([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[O:21])=[O:5])=[CH:7][C:8]=1[C:9]([CH3:18])([CH3:17])[CH2:10][C:11]([OH:16])=[O:28]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 251393606-(Ethoxy(diethylphosphonomethyl)phosphinoyl)-3,4-dihydro-4,4-dimethylchromen-2-one

Product 1

HCID 251407843-(2-Hydroxy-5-(Ethoxy(diethylphosphonomethyl)phosphinoyl)phenyl)-3-methylbutanoic acidYield 105%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 120 (0.99 g, 2.4 mmol) and KOH (0.095 g, 2.4 mmol) in methanol was stirred at room temperature for 2 hr. The solvent was removed removed under reduced pressure and the product was resuspended in water, the pH was adjusted to 4 by the addition of HCl, and the product was extracted with CH2Cl2. The organics were dried over Na2SO4, filtered and concentrated, resulting in 121 as a pale yellow oil (1.1 g, 105%) which was used without purification. 1H NMR (400 MHz, CDCl3) δ 1.26 (t, J=7.2, 3H), 1.29-1.37 (m, 6H), 1.45 (s, 3H), 1.48 (s, 3H), 2.63 (dd, J=17.7, 20.9, 2H), 2.93 (AB q, J=14.2, 2H), 4.00-4.20 (m, 6H), 6.74 (bs, 1H), 7.56 (ddd, J=1.6, 8.5, 12.2, 2H), 7.63 (d, J=13.3, 1H).

Workup

  1. customThe solvent was removed
  2. customremoved under reduced pressure
  3. additionthe pH was adjusted to 4 by the addition of HCl
  4. extractionthe product was extracted with CH2Cl2
  5. dry with materialThe organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2f3efa07a1d74d99ace72abafd9f53e4
Source dataset
uspto-grants-2013_09
Patent number
US08524691B2

Reaction notes

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