3-Hydroxybutyric Acid → (-)-3-t-Butyldimethylsilyloxybutyric acid

HRID 529970Notes

Reaction equation

HRID 529970 reaction equation
[OH:1][CH:2]([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].[CH3:8][C:9]([Si:12](Cl)([CH3:14])[CH3:13])([CH3:11])[CH3:10]>C(Cl)Cl>[C:9]([Si:12]([CH3:14])([CH3:13])[O:1][CH:2]([CH3:7])[CH2:3][C:4]([OH:6])=[O:5])([CH3:11])([CH3:10])[CH3:8]

Participants

4

Reactant 2

HCID 4413-Hydroxybutyric AcidHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 13712781(-)-3-t-Butyldimethylsilyloxybutyric acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Hydroxy-butyric acid (500 mg, 4.8 mmol) is dissolved in a mixture of TBSCl (1.5 g, 10.1 mmol) in dry DCM (48 mL). The resulting mixture is stirred overnight at room temperature. The resulting suspension is then filtered and the obtained residues are washed with DCM, then stirred in Et2O and filtered. The obtained filtrate is evaporated to give the desired product that is used as such.

Workup

  1. filtrationThe resulting suspension is then filtered
  2. washthe obtained residues are washed with DCM
  3. stirringstirred in Et2O
  4. filtrationfiltered
  5. customThe obtained filtrate is evaporated

Sources & evidence

ORD record
ord-8ecca6f1a18d463d89f9800f9d024cbd
Source dataset
uspto-grants-2016_05
Patent number
US09351955B2

Reaction notes

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