Lithium hydroxide, monohydrate → HCID 13515957, compound

HRID 407908Notes

Reaction equation

HRID 407908 reaction equation
[CH2:1]([O:8][C@H:9]([C@@H:15]([OH:21])[C:16]([O:18]CC)=[O:17])[C:10]([O:12]CC)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>C1COCC1>[CH2:1]([O:8][C@H:9]([C@@H:15]([OH:21])[C:16]([OH:18])=[O:17])[C:10]([OH:12])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 11738010HCID 11738010, compound

Product 1

HCID 13515957HCID 13515957, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2R,3R)-Diethyl 2-(benzyloxy)-3-hydroxysuccinate (15 g, 50.6 mmol) was dissolved in 30% aqueous THF (250 mL) and lithium hydroxide hydrate (4.25 g, 101 mmol) was added and the reaction stirred at ambient temperature overnight. The reaction was then partitioned between aqueous citric acid and EtOAc, dried over Na2SO4, filtered and concentrated to afford (2R,3R)-2-(benzyloxy)-3-hydroxysuccinic acid (11.5 g, 47.9 mmol, 94.6% yield) as a clear colorless oil.

Workup

  1. customThe reaction was then partitioned between aqueous citric acid and EtOAc
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4ec5ff060b1647c088f7ba77cca93cc6
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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