Methanol → HCID 53655744, compound

HRID 636019Notes

Reaction equation

HRID 636019 reaction equation
[CH3:1][CH:2]([CH3:12])[CH2:3][C@H:4]([C@H:9]([OH:11])[CH3:10])[C:5]([O:7]C)=[O:6].O.O.[OH-].[Li+].CO>C1COCC1>[CH3:1][CH:2]([CH3:12])[CH2:3][C@H:4]([C@H:9]([OH:11])[CH3:10])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 53982593HCID 53982593, compound

Product 1

HCID 53655744HCID 53655744, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Methyl (2R,3R)-2-(2-methyl-1-propyl)-3-hydroxybutanoate (7.99 g, 46 mmol) in 50 mL of THF is treated with 50 mL of water containing 3.9 g (92 mmol) of lithium hydroxide monohydrate. The reaction flask is treated with 5.0 mL of MeOH and allowed to stir for 17 h at 25° C. The mixture is partitioned between water and ether followed by separation of the aqueous layer. The aqueous solution is brought to pH 3 with 6 N aqueous hydrochloric acid and the mixture is extracted with ether. The organic phase is dried over magnesium sulfate and concentrated under reduced pressure to afford 6.6 g (90%) of (2R,3R)-2-(2-methyl-1-propyl)-3-hydroxybutanoic acid.

Workup

  1. customThe mixture is partitioned between water and ether
  2. customfollowed by separation of the aqueous layer
  3. extractionthe mixture is extracted with ether
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd35165a55984f3bbb80f00c869cb53d
Source dataset
uspto-grants-2001_02
Patent number
US06191150B1

Reaction notes

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