Water → 5-(Cyclohexyl-ethoxy-methyl)-2-(2,6-diethyl-phenyl)-4-ethoxy-pyridine

HRID 251606Notes

Reaction equation

HRID 251606 reaction equation
[H-].[Na+].[CH:3]1([CH:9]([C:11]2[CH:12]=[N:13][C:14]([C:20]3[C:25]([CH2:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:21]=3[CH2:28][CH3:29])=[CH:15][C:16]=2[O:17][CH2:18][CH3:19])[OH:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.I[CH2:31][CH3:32].O>CN(C=O)C>[CH:3]1([CH:9]([O:10][CH2:31][CH3:32])[C:11]2[C:16]([O:17][CH2:18][CH3:19])=[CH:15][C:14]([C:20]3[C:25]([CH2:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:21]=3[CH2:28][CH3:29])=[N:13][CH:12]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 59678355Cyclohexyl-[6-(2,6-diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-methanol

Product 1

HCID 596780605-(Cyclohexyl-ethoxy-methyl)-2-(2,6-diethyl-phenyl)-4-ethoxy-pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 12 mg, 0.3 mmol) is added to a solution of cyclohexyl-[6-(2,6-diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-methanol (74 mg, 0.2 mmol) in DMF (0.5 mL) at room temperature. The resulting mixture is stirred for 30 minutes. Iodoethane (31 mg, 0.2 mmol) is then added and the mixture is stirred for an additional 1 hour. Water (1 mL) is added to the above mixture and the aqueous layer is extracted with ethyl acetate (2×2 mL). The combined organic layers are dried and concentrated in vacuo. The crude product is purified with PTLC (hexanes/ethyl acetate 6:1) to give 5-(cyclohexyl-ethoxy-methyl)-2-(2,6-diethyl-phenyl)-4-ethoxy-pyridine. 1H NMR: (CDCl3) 8.50 (s, 1H), 7.28 (t, 1H), 7.12 (d, 2H), 6.70 (S, 1H), 4.45 (d, 1H), 4.03 (q, 2H), 3.34 (m, 2H), 2.34 (m, 4H), 2.02 (br, 1H), 1.73 (m, 4H), 1.21 (m, 4H), 1.05 (m, 13H).

Workup

  1. stirringthe mixture is stirred for an additional 1 hour
  2. extractionthe aqueous layer is extracted with ethyl acetate (2×2 mL)
  3. customThe combined organic layers are dried
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified with PTLC (hexanes/ethyl acetate 6:1)

Sources & evidence

ORD record
ord-bef19f8b402a4d6881c386154a0d5ea0
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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