Ammonium Chloride → HCID 70818741, compound

HRID 512094Notes

Reaction equation

HRID 512094 reaction equation
[CH3:1][O-:2].[Na+].[Na].[CH2:5]([O:12][C:13]1[C:18](I)=[C:17]([CH3:20])[N:16]=[C:15]([CH3:21])[C:14]=1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH4+].[Cl-]>[Cu]I.CO>[CH2:5]([O:12][C:13]1[C:18]([O:2][CH3:1])=[C:17]([CH3:20])[N:16]=[C:15]([CH3:21])[C:14]=1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 70819131HCID 70819131, compound

Product 1

HCID 70818741HCID 70818741, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of sodium methoxide prepared from sodium (5.0 mg, 0.23 mmol) and MeOH (1 mL) were added the iodo derivative 19 (27 mg, 0.06 mmol) and CuI (1.66 mg, 0.009 mmol). The reaction mixture was heated at 110° C. for 18 h and cooled, and 1 M aqueous NH4Cl was added. The mixture was extracted with portions of ethyl ether. The combined organic phase was dried over anhydrous MgSO4 and concentrated under diminished pressure to afford a crude residue. Elution with ethyl acetate gave 4-(benzyloxy)-3-heptyl-5-methoxy-2,6-dimethylpyridine (20) as a light yellow oil: yield 19 mg (71%); silica gel TLC Rf 0.3 (1:1 hexane/ethyl acetate); 1H NMR (CDCl3) δ 0.60-0.89 (m, 3H), 1.26-1.30 (m, 10H), 2.48 (s, 3H), 2.60-2.62 (m, 2H) 2.74 (s, 3H), 3.70 (s, 3H), 4.95 (s, 2H), 7.38-7.42 (m, 4H) and 7.53-7.56 (m, 1H).

Workup

  1. temperaturecooled
  2. extractionThe mixture was extracted with portions of ethyl ether
  3. dry with materialThe combined organic phase was dried over anhydrous MgSO4
  4. concentrationconcentrated under diminished pressure
  5. customto afford a crude residue
  6. washElution with ethyl acetate

Sources & evidence

ORD record
ord-5079fe4369ce41bfaa1b6b8b75e2630d
Source dataset
uspto-grants-2015_08
Patent number
US09102626B2

Reaction notes

Loading…