2-Bromo-2-methylpropanoyl cyanide → 5-(4-(benzyloxy)phenyl)-4-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one

HRID 655369Notes

Reaction equation

HRID 655369 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:25])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].Br[C:33]([CH3:39])([CH3:38])[C:34](C#N)=[O:35]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:25][C:33]([CH3:39])([CH3:38])[C:34](=[O:35])[C:16]=2[C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 124878382-Bromo-2-methylpropanoyl cyanideHCID 189237831-(4-(Benzyloxy)phenyl)-2-(4-methoxyphenyl)ethanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 593547815-(4-(benzyloxy)phenyl)-4-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-oneYield 4.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a pre-cooled 0° C. solution of 1-(4-(benzyloxy)phenyl)-2-(4-methoxyphenyl)-ethanone (2 g, 6.02 mmol) in THF (20 mL) under an inert atmosphere was added t-BuOK (8 mL, 1.0 N solution in THF). The mixture was then stirred for 30 minutes. 2-Bromo-2-methylpropanoyl cyanide (2 g, 12 mmol) was then added to then reaction mixture and stirring was continued for an additional 16 h. The reaction mixture was then 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), and then dried over Na2SO4 concentrated and purified via silica gel column chromatography (10-15% Ethyl acetate in hexanes) to afford 5-(4-(benzyloxy)phenyl)-4-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (100 mg) as a white solid.

Workup

  1. customreaction mixture
  2. stirringstirring
  3. waitwas continued for an additional 16 h
  4. customThe reaction mixture was then quenched with cold water (10 mL)
  5. extractionextracted with EtOAc (2×50 mL)
  6. washThe combined organic layers were washed with water (30 mL) and brine (30 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. custompurified via silica gel column chromatography (10-15% Ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5d46e2f4302c4990aaf4a81c197284aa
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

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