Ammonium Chloride → Cyclohexyl-[6-(2,6-diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-methanol

HRID 1392637Notes

Reaction equation

HRID 1392637 reaction equation
[CH:1]1([Mg]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH3:18])[C:12]=1[C:19]1[N:24]=[CH:23][C:22]([CH:25]=[O:26])=[C:21]([O:27][CH2:28][CH3:29])[CH:20]=1)[CH3:10].[Cl-].[NH4+]>CCOCC>[CH:1]1([CH:25]([C:22]2[CH:23]=[N:24][C:19]([C:12]3[C:13]([CH2:17][CH3:18])=[CH:14][CH:15]=[CH:16][C:11]=3[CH2:9][CH3:10])=[CH:20][C:21]=2[O:27][CH2:28][CH3:29])[OH:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 596782676-(2,6-Diethyl-phenyl)-4-ethoxy-pyridine-3-carbaldehydeHCID 178478990HCID 178478990, compound

Product 1

HCID 59678355Cyclohexyl-[6-(2,6-diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A cyclohexylmagnesium chloride solution (2 M in THF, 1 mL) is slowly added to a solution of 6-(2,6-diethyl-phenyl)-4-ethoxy-pyridine-3-carbaldehyde (prepared as described above) (142 mg, 0.5 mmol) in ether (2 mL) at 0° C., and the resulting mixture is stirred at room temperature for 30 minutes. Saturated ammonium chloride solution (1 mL) is added to quench the reaction. The organic layer is separated and dried over anhydrous Na2SO4. The solvents are removed in vacuo and the crude is purified with PTLC (hexanes/ethyl acetate 3:1) to give cyclohexyl-[6-(2,6-diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-methanol. 1H NMR: (CDCl3) 8.40 (s, 1H), 7.28 (t, 1H), 7.16 (d, 2H), 6.76 (S, 1H), 4.54 (t, 1H), 4.08 (q, 2H), 2.32 (m, 4H), 2.05 (br, 1H), 1.75 (m, 4H), 1.40 (m, 4H), 1.05 (m, 10H).

Workup

  1. customto quench
  2. customthe reaction
  3. customThe organic layer is separated
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvents are removed in vacuo
  6. customthe crude is purified with PTLC (hexanes/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-daabf8b669cc4d21b43f28dfb10aa2be
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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