2-Bromo-2-methylpropanoyl cyanide → 5-(4-methoxyphenyl)-2,2-dimethyl-4-(4-(quinolin-2-ylmethoxy)phenyl)furan-3(2H)-one

HRID 1258283Notes

Reaction equation

HRID 1258283 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:29])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.Br[C:31]([CH3:37])([CH3:36])[C:32](C#N)=[O:33]>C1COCC1.CC([O-])(C)C.[K+]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:29][C:31]([CH3:37])([CH3:36])[C:32](=[O:33])[C:10]=2[C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)=[CH:15][CH:16]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 124878382-Bromo-2-methylpropanoyl cyanideHCID 593548091-(4-Methoxyphenyl)-2-(4-(quinolin-2-ylmethoxy)phenyl)ethanone

Product 1

HCID 445944685-(4-methoxyphenyl)-2,2-dimethyl-4-(4-(quinolin-2-ylmethoxy)phenyl)furan-3(2H)-oneYield 8.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 23665647Potassium tert-butoxideSolvent

Procedure

To a room temperature, stirred solution of 1-(4-methoxyphenyl)-2-(4-(quinolin-2-ylmethoxy)phenyl)ethanone (100 mg, 0.26 mmol) in THF (5 mL), t-BuOK (1.0 mL, 1.0 N solution in THF) was added under an inert atmosphere and the resulting mixture was stirred for 30 min 2-Bromo-2-methylpropanoyl cyanide (90 mg, 0.5 mmol) was then added to the reaction mixture and stirring was continued for an additional 16 h. The reaction mixture was quenched with cold water (10 mL) and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water (30 mL) and brine (30 mL), dried over Na2SO4, filtered, concentrated and purified by column chromatography (10-15% ethyl acetate in hexanes) to afford 5-(4-methoxyphenyl)-2,2-dimethyl-4-(4-(quinolin-2-ylmethoxy)phenyl)furan-3(2H)-one (10 mg) as a solid.

Workup

  1. additionwas added under an inert atmosphere
  2. additionwas then added to the reaction mixture
  3. customThe reaction mixture was quenched with cold water (10 mL)
  4. extractionextracted with EtOAc (2×50 mL)
  5. washThe combined organic layers were washed with water (30 mL) and brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by column chromatography (10-15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b6f598ff6f6149d4b0dccb2c5f91984e
Source dataset
uspto-grants-2013_06
Patent number
US08466148B2

Reaction notes

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