Toluene → HCID 68379265, compound

HRID 403479Notes

Reaction equation

HRID 403479 reaction equation
C1(C)C=CC=CC=1.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]#[N:18])=[CH:11][CH:10]=1.[C:19](OCC)(=[O:22])[CH2:20][CH3:21]>C1COCC1>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]([C:19](=[O:22])[CH2:20][CH3:21])[C:17]#[N:18])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7749Ethyl PropionateHCID 27356113-(4-Bromophenyl)propionitrile

Product 1

HCID 68379265HCID 68379265, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.7 M solution of potassium tert. pentylate in toluene (81 ml, 139 mmol) was added dropwise to a solution of 3-(4-bromo-phenyl)-propionitrile (9.70 g, 46.2 mmol) in 200 ml of THF at rt, followed by addition of ethyl propionate (18.9 ml, 185 mmol). Stirring was continued for 20 min. The reaction mixture was quenched by careful addition of 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2 SO4 and evaporated. The residue was purified by column chromatography (silica gel, EtOAc/n-hexane 3:7) to yield 1 as a yellow oil.

Workup

  1. customThe reaction mixture was quenched by careful addition of 1N hydrochloric acid
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. customdried over Na2 SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography (silica gel, EtOAc/n-hexane 3:7)

Sources & evidence

ORD record
ord-7fe4405ec53048b993c272cd0911fc73
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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