Potassium Hydroxide → 3-(5-Trimethylsilyl-3-furyl)propionic acid

HRID 345896Notes

Reaction equation

HRID 345896 reaction equation
[OH-].[K+].[CH3:3][Si:4]([CH3:17])([CH3:16])[C:5]1[O:9][CH:8]=[C:7]([CH2:10][CH2:11][C:12]([O:14]C)=[O:13])[CH:6]=1>C(O)C.O>[CH3:17][Si:4]([CH3:3])([CH3:16])[C:5]1[O:9][CH:8]=[C:7]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:6]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19019871Methyl 3-(5-trimethylsilyl-3-furyl)propionate

Product 1

HCID 199916153-(5-Trimethylsilyl-3-furyl)propionic acid

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent2×

Procedure

A solution of potassium hydroxide (446 mg, 7.96 mmol) in 95% ethanol/water (4 ml) was added to a solution of methyl 3-(5-trimethylsilyl-3-furyl)propionate(1.2 g, 5.3 mmol), prepared as in Example 2, in 95% ethanol/water (4ml) at 0°. After stirring at 0° for 5 hours and at room temperature for 5 hours, most of the solvent was evaporated. The residue was dissolved in ethyl acetate (15 ml), acidified with hydrochloric acid and the mixture then extracted thoroughly with ethyl acetate. Evaporation of the dried (magnesium sulfate) extracts gave an oil, which on crystallization from hexane (-78°) gave the title acid as colorless needles, mp ca. 25°.

Workup

  1. customwas evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate (15 ml)
  3. extractionthe mixture then extracted thoroughly with ethyl acetate
  4. customEvaporation of the
  5. dry with materialdried (magnesium sulfate)
  6. customextracts gave an oil, which
  7. customon crystallization from hexane (-78°)
  8. customgave the title acid as colorless needles, mp ca. 25°

Sources & evidence

ORD record
ord-c2b4923fba9344219e2024f284041cc5
Source dataset
uspto-grants-1991_10
Patent number
US05059611

Reaction notes

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