Ammonium Chloride → 1-[6-(2,6-Diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-butan-1-ol

HRID 251614Notes

Reaction equation

HRID 251614 reaction equation
[CH2:1]([Mg]Cl)[CH2:2][CH3:3].[CH2:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH3:15])[C:9]=1[C:16]1[N:21]=[CH:20][C:19]([CH:22]=[O:23])=[C:18]([O:24][CH2:25][CH3:26])[CH:17]=1)[CH3:7].[NH4+].[Cl-]>CCOCC>[CH2:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH3:15])[C:9]=1[C:16]1[N:21]=[CH:20][C:19]([CH:22]([OH:23])[CH2:1][CH2:2][CH3:3])=[C:18]([O:24][CH2:25][CH3:26])[CH:17]=1)[CH3:7]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 596782676-(2,6-Diethyl-phenyl)-4-ethoxy-pyridine-3-carbaldehydeHCID 178455855HCID 178455855, compound

Product 1

HCID 596783161-[6-(2,6-Diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-butan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of PrMgCl (2M in ether, 0.15 mL) is added dropwise to a solution of 6-(2,6-diethyl-phenyl)-4-ethoxy-pyridine-3-carbaldehyde (100 mg, 0.59 mmol) in ether (5 mL) at room temperature. After the mixture is stirred for 2 hours, aqueous NH4Cl solution (10 mL) is added and the organic layer is separated. The aqueous layer is extracted with ether (1×) and the organic layers are combined, dried and concentrated in vacuo. The residue is purified by PTLC purification (4:1 hexane/EtOAc) to give 1-[6-(2,6-diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-butan-1-ol. 1H NMR (CDCl3) 8.48 (s, 1H), 7.26 (t, 1H), 7.12 (d, 2H), 6.74 (s, 1H), 4.90 (s, 1H), 4.08 (q, 2H), 2.70 (s, 1H), 2.33 (m, 4H), 1.85 (m, 2H), 1.30-1.60 (m, 5H), 0.90-1.05 (m, 9H).

Workup

  1. customthe organic layer is separated
  2. extractionThe aqueous layer is extracted with ether (1×)
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by PTLC purification (4:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-df51b0a8f84f4576818b73fc7f063bd3
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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