Bromoacetonitrile → 7-Cyano-5-oxoheptanoic acid

HRID 1494151Notes

Reaction equation

HRID 1494151 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[K+].[O:11]=[C:12]([CH3:19])[CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17].Br[CH2:21][C:22]#[N:23]>O1CCCC1>[C:22]([CH2:21][CH2:19][C:12](=[O:11])[CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])#[N:23]

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 184074-Acetylbutyric acidHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 149867127-Cyano-5-oxoheptanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of potassium hexamethyldisilazide (66 mL, 60 mmol) in dry tetrahydrofuran (140 mL) at -70° C. is added slowly 5-oxohexanoic acid (36 mL, 30 mmol). The resulting yellow suspension is stirred at -70° C. for 1 hour and bromoacetonitrile (2.2 mL, 32 mmol) is added slowly. The reaction mixture is stirred at -70° C. for 1 hour and then at room temperature for 0.5 hour. The reaction is quenched by addition of 1N aqueous hydrochloric acid (100 mL). The aqueous layer is extracted twice with ether. Combined organic layer is dried, filtered and evaporated to obtain a dark oil which is purified by silica gel chromatography using 9:1 ether:hexane with 1% acetic acid as eluent to give 7-cyano-5-oxoheptanoic acid as an oil.

Workup

  1. stirringThe reaction mixture is stirred at -70° C. for 1 hour
  2. waitat room temperature for 0.5 hour
  3. customThe reaction is quenched by addition of 1N aqueous hydrochloric acid (100 mL)
  4. extractionThe aqueous layer is extracted twice with ether
  5. customCombined organic layer is dried
  6. filtrationfiltered
  7. customevaporated
  8. customto obtain a dark oil which
  9. customis purified by silica gel chromatography

Sources & evidence

ORD record
ord-ba1daed8b3624635b6cffe2d6b97c8b8
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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