Tetrapropylammonium → HCID 18922186, compound

HRID 1871940Notes

Reaction equation

HRID 1871940 reaction equation
Br[C:2]1[CH:12]=[CH:11][C:5]2[O:6][CH2:7][C:8]([CH3:10])([CH3:9])[C:4]=2[CH:3]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19]=[O:20].C([N+]([CH2:31][CH2:32][CH3:33])(CCC)CCC)CC.[CH3:34][N+]1([O-])CCOCC1>CCOCC.CCCCCC>[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([C:2]1[CH:12]=[C:11]([C:32]([CH3:33])([CH3:34])[CH3:31])[C:5]2[O:6][CH2:7][C:8]([CH3:10])([CH3:9])[C:4]=2[CH:3]=1)=[O:20]

Participants

7

Reactant 4

HCID 9559TetrapropylammoniumHCID 142732-PyridinecarboxaldehydeHCID 82029Methyl morpholine oxideHCID 53235955-Bromo-3,3-dimethyl-2,3-dihydro-1-benzofuran

Product 1

HCID 18922186HCID 18922186, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent2×

Procedure

To 1.0 g (3.5 mmol) of a stirring solution of 5-bromo-2,3-dihydro-3,3-dimethylbenzo[b]furan in 2.0 mL of ether and 18 mL of dry hexane at -78° C. is added 4.4 mL (7.1 mmol) of t-butylithium in hexane. The resulting mixture is stirred for 40 min, then 0.5 g (4.6 mmol) of 2-pyridinecarboxaldehyde is added. The reaction is allowed to slowly reach RT and is then quenched with water. The reaction is then diluted with 50 mL of ether, and the organic layer is separated. The remaining aqueous layer is extracted with ether (3×20 mL). The organic layers are then combined, dried over MgSO4, filtered, and the solvent was removed in vacuo. The residue is dissolved in 20 mL CH2Cl2, and to this solution was added 0.1 g (0.4 mmol) of tetrapropylammonium perruthinate followed by 0.6 g (5.3 mmol) of N-methyl morpholine-N-oxide at RT. The reaction is stirred for 3 h, then filtered through silica gel, and the solvent is removed in vacuo. Purification by sgc with 1 ethyl acetate:5 hexane resultes in about 0.30 g (29%) of a yellow solid. mp 95-97° C.

Workup

  1. customis allowed to slowly reach RT
  2. customis then quenched with water
  3. additionThe reaction is then diluted with 50 mL of ether
  4. customthe organic layer is separated
  5. extractionThe remaining aqueous layer is extracted with ether (3×20 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. dissolutionThe residue is dissolved in 20 mL CH2Cl2
  10. stirringThe reaction is stirred for 3 h
  11. filtrationfiltered through silica gel
  12. customthe solvent is removed in vacuo
  13. customPurification by sgc with 1 ethyl acetate

Sources & evidence

ORD record
ord-fd1a13045ac84cc88829bfbcf5fce02f
Source dataset
uspto-grants-2000_08
Patent number
US06107311

Reaction notes

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