Iodoethane → HCID 59678115, compound

HRID 1392636Notes

Reaction equation

HRID 1392636 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH3:12])[C:6]=1[C:13]1[N:18]=[CH:17][C:16]([CH:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[OH:20])=[C:15]([O:27][CH3:28])[CH:14]=1)[CH3:4].I[CH2:30][CH3:31].[NH4+].[Cl-]>CN(C=O)C.CCCCCC>[CH2:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([CH2:3][CH3:4])[C:6]=1[C:13]1[CH:14]=[C:15]([O:27][CH3:28])[C:16]([CH:19]([O:20][CH2:30][CH3:31])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:17][N:18]=1)[CH3:12]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59678346HCID 59678346, compound

Product 1

HCID 59678115HCID 59678115, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

NaH (60% in mineral oil, 8 mg) is added to a solution of [6-(2,6-diethyl-phenyl)-4-methoxy-pyridin-3-yl]-phenyl-methanol (18 mg) in DMF (1 mL). The resulting mixture is stirred at room temperature for 15 minutes. The mixture is then treated with iodoethane (20 mg) and stirred at the same temperature for 1 hour. Aqueous NH4Cl solution (5 mL) and hexane (5 mL) are added to the mixture. The organic layer is separated, dried, and concentrated in vacuo. The crude product is purified by PTLC (4:1 hexane/EtOAc) to give 2-(2,6-diethyl-phenyl)-5-(ethoxy-phenyl-methyl)-4-methoxy-pyridine. 1H NMR (CDCl3) 8.66 (s, 1H), 7.45 (d, 2H), 7.35 (t, 2H), 7.26 (m, 2H), 7.14 (m, 2H), 6.71 (s, 1H), 5.74 (s, 1H), 3.80 (s, 3H), 3.56 (q, 2H), 2.33 (m, 4H), 1.27 (t, 3H), 1.05 (m, 6H).

Workup

  1. stirringstirred at the same temperature for 1 hour
  2. customThe organic layer is separated
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by PTLC (4:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-25a465ff124f482eb6ccb8a7f61b14f7
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

Loading…