Ammonium Chloride → HCID 59678346, compound

HRID 251603Notes

Reaction equation

HRID 251603 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH3:17])[C:11]=1[C:18]1[N:23]=[CH:22][C:21]([CH:24]=[O:25])=[C:20]([O:26][CH3:27])[CH:19]=1)[CH3:9].[NH4+].[Cl-]>CCOCC>[CH2:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH3:17])[C:11]=1[C:18]1[N:23]=[CH:22][C:21]([CH:24]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[OH:25])=[C:20]([O:26][CH3:27])[CH:19]=1)[CH3:9]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86593984HCID 86593984, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 59678346HCID 59678346, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Phenyllithium (1M in THF, 0.26 mL) is added dropwise to a solution of 6-(2,6-diethyl-phenyl)-4-methoxy-pyridine-3-carbaldehyde (70 mg, 0.26 mmol) in ether (4 mL) at room temperature. The mixture is stirred for 2 hours, then treated with aqueous NH4Cl solution (4 mL) and diluted with ether (10 mL). The organic layer is separated, dried and concentrated. The crude is purified by PTLC (4:1 hexane/EtOAc) to give [6-(2,6-diethyl-phenyl)-4-methoxy-pyridin-3-yl]-phenyl-methanol. 1H NMR (CDCl3) 8.51 (s, 1H), 7.26-7.43 (m, 6H), 7.15 (d, 2H), 6.76 (s, 1H), 6.06 (s, 1H), 3.82 (s, 3H), 3.21 (s, 1H), 2.32 (m, 4H), 1.05 (m, 6H).

Workup

  1. customThe organic layer is separated
  2. customdried
  3. concentrationconcentrated
  4. customThe crude is purified by PTLC (4:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-03d282e458474391b874bc0d9c7655e8
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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