Carbon Dioxide → 3-(Trimethylsilyl)butanoic acid

HRID 1735172Notes

Reaction equation

HRID 1735172 reaction equation
BrC[CH2:3][CH2:4][Si:5]([CH3:8])([CH3:7])[CH3:6].[Mg].[C:10](=[O:12])=[O:11].[CH3:13]COCC>>[CH3:6][Si:5]([CH3:8])([CH3:7])[CH:4]([CH3:13])[CH2:3][C:10]([OH:12])=[O:11]

Participants

5

Reactant 4

HCID 280Carbon DioxideHCID 3283Diethyl Ether2×HCID 5462224MagnesiumHCID 128458003-Bromopropyltrimethylsilane

Product 1

HCID 194370223-(Trimethylsilyl)butanoic acid

Procedure

A solution containing 3 g (15.4 mmol) of (3-bromopropyl)trimethylsilane in 3 ml of dry ether was added to 0.375 g (15.4 mmol) of magnesium turnings in ether (40 ml final volume of solution). After 1 hour of reflux gazeous carbondioxide was bubbled through the reaction mixture (3 g, 77 mmol of dry ice). After 2 hours of stirring at room temperature the reaction mixture was partitioned between aqueous ammonium chloride and ether. The organic phase was separated, the aqueous phase was further acidified with hydrochloric acid 1N and extracted with ether. Ethereal phases were pooled and the solvent was removed under reduced pressure. Separation of the expected 4-trimethylsilyl-butanoic acid from dimer of starting (3-bromopropyl)trimethylsilane was finally performed by acid base extraction. 0.62 g of 3-(trimethylsilyl)-butanoic acid was isolated as a colorless liquid.

Workup

  1. customwas partitioned between aqueous ammonium chloride and ether
  2. customThe organic phase was separated
  3. extractionextracted with ether
  4. customthe solvent was removed under reduced pressure
  5. customSeparation of the expected 4-trimethylsilyl-butanoic acid from dimer of starting (3-bromopropyl)trimethylsilane
  6. extractionwas finally performed by acid base extraction

Sources & evidence

ORD record
ord-93d3d9900d134dd1922301639c5f8877
Source dataset
uspto-grants-1996_07
Patent number
US05536732

Reaction notes

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