4-(Chloromethyl)pyridine → 3-(Benzhydrylidene-amino)-3-pyridin-4-ylmethyl-dihydro-furan-2-one

HRID 1421910Notes

Reaction equation

HRID 1421910 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11](=[N:24][CH:25]1[CH2:29][CH2:28][O:27][C:26]1=[O:30])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[N:31]1[CH:36]=[CH:35][C:34]([CH2:37]Cl)=[CH:33][CH:32]=1>C1COCC1>[C:11](=[N:24][C:25]1([CH2:37][C:34]2[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=2)[CH2:29][CH2:28][O:27][C:26]1=[O:30])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 745714-(Chloromethyl)pyridineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 132309163-[(diphenylmethylene)amino]dihydrofuran-2(3H)-one

Product 1

HCID 541390243-(Benzhydrylidene-amino)-3-pyridin-4-ylmethyl-dihydro-furan-2-oneYield 49.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-40 °C

Procedure

Potassium bis-(trimethylsilyl)amide (2.67, 13.4 mMol) was dissolved in anhydrous THF (50 mL) under an atmosphere of dry N2. The mixture was cooled to -40° C. to which was added a solution of 3-(benzhydrylidene-amino)-dihydro-furan-2-one (3.38 g, 12.7 mMol) in THF (30 mL). The mixture was warmed to ambient temperature and stirred at this temperature for 30 minutes. The solution was then cooled to -40° C. and a solution of 4-picolyl chloride (1.70 g, 13.4 mMol) in THF (20 mL) was added. The reaction mixture was warmed to ambient temperature and stirred for 18 hours. The mixture was partitioned between ethyl acetate-(EtOAc) and water. The organic layer was dried over sodium sulfate (Na2SO4), filtered and concentrated under vacuum to give a yellow oil. The oil was chromatographed on flash silica gel eluting with a gradient of EtOAc-hexanes (50:50) to EtOAc-hexanes (60:40 ) to give 2.26 g of the titled compound as an oil which crystallizes to a white solid upon standing.

Workup

  1. temperatureThe mixture was warmed to ambient temperature
  2. temperatureThe solution was then cooled to -40° C.
  3. temperatureThe reaction mixture was warmed to ambient temperature
  4. stirringstirred for 18 hours
  5. customThe mixture was partitioned between ethyl acetate-(EtOAc) and water
  6. dry with materialThe organic layer was dried over sodium sulfate (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customto give a yellow oil
  10. customThe oil was chromatographed on flash silica gel eluting with a gradient of EtOAc-hexanes (50:50) to EtOAc-hexanes (60:40 )

Sources & evidence

ORD record
ord-6ed05d495d274515b80b41c738812580
Source dataset
uspto-grants-2000_06
Patent number
US06080769

Reaction notes

Loading…