Water → 3,3-Dimethoxypropanoic acid lithium salt

HRID 10110Notes

Reaction equation

HRID 10110 reaction equation
C[O:2][C:3](=[O:10])[CH2:4][CH:5]([O:8][CH3:9])[O:6][CH3:7].O[Li:12].O.O>C1COCC1>[Li+:12].[CH3:7][O:6][CH:5]([O:8][CH3:9])[CH2:4][C:3]([O-:10])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 81924Methyl 3,3-dimethoxypropionateHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 876652803,3-Dimethoxypropanoic acid lithium saltYield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Related to methods described in Alabaster, C. T. et. al., J. Med. Chem. 1988, 31, 2048–2056.) 3,3-Dimethoxypropanoic acid methyl ester (14.25 g, 96.2 mmol) in THF (100 mL) was treated with LiOH.H2O (2.5 g, 106 mmol) and H2O (2 mL). The mixture was brought to reflux for 4 hours, cooled to room temperature and azeotropically dried from THF (4 times) to provide white solids (13.3 g).

Workup

  1. temperatureto reflux for 4 hours
  2. dry with materialazeotropically dried from THF (4 times)

Sources & evidence

ORD record
ord-1760007316da4df791d25f5e9c52543d
Source dataset
uspto-grants-2006_08
Patent number
US07091372B2

Reaction notes

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