Lithium hydroxide, monohydrate → HCID 53959927, compound

HRID 636004Notes

Reaction equation

HRID 636004 reaction equation
[CH3:1][CH:2]([CH3:14])[CH2:3][C@H:4]([C@H:9]([OH:13])[CH2:10][CH2:11][CH3:12])[C:5]([O:7]C)=[O:6].O.[OH-].[Li+].S([O-])(O)(=O)=O.[Na+]>O.CO.C1COCC1>[CH3:14][CH:2]([CH3:1])[CH2:3][C@H:4]([C@H:9]([OH:13])[CH2:10][CH2:11][CH3:12])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 516919Sodium BisulfateHCID 53980481HCID 53980481, compound

Product 1

HCID 53959927HCID 53959927, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of methyl (2R,3R)-2-(2-methyl-1-propyl)-3-hydroxyhexanoate (6.5 g, 31.9 mmol) in 100 mL of water—MeOH—THF (1:1:4) is treated with lithium hydroxide monohydrate (1.6 g, 38 mmol) and stirred overnight. The reaction mixture is acidified to pH 2 using 1 M aqueous sodium hydrogen sulfate and extracted with two 100-mL portions of EtOAc. The combined organic layers are washed with two 25-mL portions of saturated aqueous sodium chloride, dried over sodium sulfate and filtered, and the solvents are removed under reduced pressure. Purification by flash chromatography on silica gel eluting with 10% EtOAc-hexanes affords 6.0 g (100%) of (2R,3R)-2-(2-methyl-1-propyl)-3-hydroxyhexanoic acid as a gum.

Workup

  1. extractionextracted with two 100-mL portions of EtOAc
  2. washThe combined organic layers are washed with two 25-mL portions of saturated aqueous sodium chloride
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvents are removed under reduced pressure
  6. customPurification by flash chromatography on silica gel eluting with 10% EtOAc-hexanes

Sources & evidence

ORD record
ord-4111beed4ce5491d9e2ed3594d1f8dad
Source dataset
uspto-grants-2001_02
Patent number
US06191150B1

Reaction notes

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