Sodium Hydroxide → HCID 54154673, compound

HRID 565238Notes

Reaction equation

HRID 565238 reaction equation
C[Si](C)(C)[C:3]#[C:4][CH2:5][C@H:6]([C@H:11]([OH:13])[CH3:12])[C:7]([O:9]C)=[O:8].[OH-].[Na+]>C1COCC1.CO>[CH2:5]([C@H:6]([C@H:11]([OH:13])[CH3:12])[C:7]([OH:9])=[O:8])[C:4]#[CH:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57259491HCID 57259491, compound

Product 1

HCID 54154673HCID 54154673, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of methyl (2R,3R)-2-(3-trimethylsilyl-2-propyne-1-yl)-3-hydroxybutanoate (5.6 g, 24.56 mmol) in THF-methanol (3:1, 160 mL) is added 2 M aqueous sodium hydroxide solution (40 mL, 36.8 mmol). The solution is stirred at 23° C. for 20 h, then concentrated and extracted with hexanes (100 mL). The aqueous layer is acidified to pH=3 with 1 M HCl and is extracted with two 100 mL portions of ethyl acetate. The combined organic layers are dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide (2R,3R)-2-(2-propyne-1-yl)-3-hydroxybutanoic acid as an oil (3.0 g, 86% yield).

Workup

  1. concentrationconcentrated
  2. extractionextracted with hexanes (100 mL)
  3. extractionis extracted with two 100 mL portions of ethyl acetate
  4. dry with materialThe combined organic layers are dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-359036192a324085b69c6f3fdcf85584
Source dataset
uspto-grants-2001_01
Patent number
US06172064B2

Reaction notes

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