Hydrochloric Acid → Ethyl 4-trimethylsilyl-3-cyanobutanoate

HRID 341336Notes

Reaction equation

HRID 341336 reaction equation
[C:1]([C:3]([CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])C(OCC)=O)#[N:2].O.[Br-].[Li+].Cl>CN(C)C=O>[CH3:19][Si:16]([CH3:17])([CH3:18])[CH2:15][CH:3]([C:1]#[N:2])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 82050Lithium BromideHCID 71530806Diethyl 2-cyano-2-(trimethylsilylmethyl)succinate

Product 1

HCID 71530807Ethyl 4-trimethylsilyl-3-cyanobutanoateYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A solution of diethyl 2-cyano-2-(trimethylsilylmethyl)succinate (592 mg, 2.08 mmol) in dimethylformamide (DMF, 5 ml) was added with water (45 μl, 2.50 mmol) and lithium bromide (217 mg, 2.49 mmol), and the mixture was stirred at 150° C. for 15 hours. The reaction mixture was cooled on ice, and added with aqueous hydrochloric acid (1 N), and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and then dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel chromatography [hexane/ethyl acetate (14:1)] to obtain ethyl 4-trimethylsilyl-3-cyanobutanoate (404 mg, 91%) mentioned in the title as colorless oil.

Workup

  1. temperatureThe reaction mixture was cooled on ice
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel chromatography [hexane/ethyl acetate (14:1)]

Sources & evidence

ORD record
ord-1f3d300b4af94f09892317d660713c12
Source dataset
uspto-grants-2014_11
Patent number
US08895769B2

Reaction notes

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