Lithium Hydroxide → HCID 11344845, compound

HRID 1430889Notes

Reaction equation

HRID 1430889 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][O:8][C@@H:9]([CH3:14])[C:10]([O:12]C)=[O:11])=[CH:5][CH:4]=1.[OH-].[Li+]>C1COCC1.CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C@@H:9]([CH3:14])[C:10]([OH:12])=[O:11])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 15907471HCID 15907471, compound

Product 1

HCID 11344845HCID 11344845, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl 2-((4-methoxybenzyl)oxy)propanoate (1 g, 4.46 mmol) in THF (20 mL) and MeOH (6 mL) at 0° C. was added lithium hydroxide (0.225 g, 9.38 mmol) and stirred for 3 h. then warmed to room temperature in 30 min. After completion of starting material (by TLC), reaction mixture was concentrated and the resultant residue was taken EtOAc (100 ml), acidified by 1.5N HCl (up to pH 1) and extracted into EtOAc (2×100 ml). Combined organic extracts were dried over anhydrous Na2SO4, concentrated to give (S)-2-((4-methoxybenzyl)oxy)propanoic acid (0.6 g) was obtained as a gummy liquid.

Workup

  1. customAfter completion of starting material (by TLC), reaction mixture
  2. concentrationwas concentrated
  3. extractionextracted into EtOAc (2×100 ml)
  4. dry with materialCombined organic extracts were dried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-58778ec91c3e4027a898d4ac5c69e525
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

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