Iodoethane → HCID 59678173, compound

HRID 251610Notes

Reaction equation

HRID 251610 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]([OH:23])[CH2:20][CH2:21][CH3:22])=[C:15]([O:24][CH3:25])[CH:14]=1)[CH3:4].I[CH2:27][CH3:28].[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O>[CH2:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH3:12])[C:6]=1[C:13]1[CH:14]=[C:15]([O:24][CH3:25])[C:16]([CH:19]([O:23][CH2:27][CH3:28])[CH2:20][CH2:21][CH3:22])=[CH:17][N:18]=1)[CH3:4]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59678216HCID 59678216, compound

Product 1

HCID 59678173HCID 59678173, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

NaH (60% in mineral oil, 12 mg) is added to a solution of 1-[6-(2,6-diethyl-phenyl)-4-methoxy-pyridin-3-yl]-butan-1-ol (24 mg) (see Example 10) in DMF (1 mL). The resulting mixture is stirred at room temperature for 15 minutes. The mixture is then treated with iodoethane (36 mg) and stirred at the same temperature for one hour. Aqueous NH4Cl solution (5 mL) and EtOAc (5 mL) are added to the mixture. The organic layer is separated, dried, and concentrated in vacuo. The crude is purified by PTLC (4:11 hexane/EtOAc) to give 2-(2,6-diethyl-phenyl)-5-(1-ethoxy-butyl)-4-methoxy-pyridine. 1H NMR (CDCl3) 8.54 (s, 1H), 7.29 (t, 1H), 7.14 (d, 2H), 6.74 (s, 1H), 4.68 (m, 1H), 3.83 (s, 3H), 3.41-3.50 (m, 2H), 2.35 (m, 4H), 1.74 (m, 2H), 1.30-1.40 (m, 2H), 1.23 (t, 3H), 1.06 (t, 6H), 0.98 (t, 3H).

Workup

  1. stirringstirred at the same temperature for one hour
  2. customThe organic layer is separated
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe crude is purified by PTLC (4:11 hexane/EtOAc)

Sources & evidence

ORD record
ord-2717854cadbb40c9b3c9c4522a308eec
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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