Lithium hydroxide, monohydrate → HCID 54234541, compound

HRID 1369274Notes

Reaction equation

HRID 1369274 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][P:14]([O:20][CH:21]([CH3:23])[CH3:22])([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])=[C:8]([P:24]([O:29][CH2:30][CH3:31])([O:26][CH2:27][CH3:28])=[O:25])[CH:7]=1.O[Li].O>C1COCC1.O>[CH2:27]([O:26][P:24]([C:8]1[CH:7]=[C:6]([CH2:5][CH2:4][C:3]([OH:32])=[O:2])[CH:11]=[CH:10][C:9]=1[O:12][CH2:13][P:14]([O:16][CH:17]([CH3:18])[CH3:19])([O:20][CH:21]([CH3:22])[CH3:23])=[O:15])([O:29][CH2:30][CH3:31])=[O:25])[CH3:28]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 53999287HCID 53999287, compound

Product 1

HCID 54234541HCID 54234541, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-(3-Diethylphosphono-4-diisopropylphosphonomethoxyphenyl)propionic acid methyl ester (474 mg, 0.96 mmol) in 5 mL THF at 0° C. was added LiOH.H2O (60 mg, 1.43 mmol) in 1 mL H2O. The reaction mixture was stirred at 0° C. for 1 hr. THF was removed in vacuo and 5 mL 1N HCl was added. Aqueous phase was extracted with DCM (8×10 mL). Combined organic was dried over Na2SO4, concentrated to yield crude product 400 mg (yield 87%) as a clear oil. Electrospray mass spectrum: m/z 479.50 (M−H).

Workup

  1. customTHF was removed in vacuo and 5 mL 1N HCl
  2. additionwas added
  3. extractionAqueous phase was extracted with DCM (8×10 mL)
  4. dry with materialCombined organic was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-166f86e74af24030bb13ecb9dd90e41a
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

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