m-Chloroperbenzoic acid → HCID 59678222, compound

HRID 251634Notes

Reaction equation

HRID 251634 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[N:16]=[C:15]([CH3:17])[C:14]([CH2:18][O:19][C:20]2[CH:25]=[C:24]([CH:26]([CH3:28])[CH3:27])[CH:23]=[CH:22][C:21]=2[CH3:29])=[C:13]([O:30][CH:31]([CH3:33])[CH3:32])[CH:12]=1)[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:39]>C(Cl)Cl>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[N+:16]([O-:39])=[C:15]([CH3:17])[C:14]([CH2:18][O:19][C:20]2[CH:25]=[C:24]([CH:26]([CH3:27])[CH3:28])[CH:23]=[CH:22][C:21]=2[CH3:29])=[C:13]([O:30][CH:31]([CH3:33])[CH3:32])[CH:12]=1)[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66993664HCID 66993664, compound

Product 1

HCID 59678222HCID 59678222, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 6-(2,6-diethyl-phenyl)-4-isopropoxy-3-(5-isopropyl-2-methyl-phenoxymethyl)-2-methyl-pyridine (250 mg, 0.56 mmol) and 3-chloroperoxy-benzoic acid (77%, 150 mg, 0.67 mmol) in CH2Cl2 (10 mL) is stirred at room temperature for 2 hours. The mixture is diluted with CH2Cl2 (20 mL) and washed with saturated Na2CO3, brine dried over sodium sulfate, and concentrated in vacuo. The residue is purified on PTLC (1:1 hexane EtOAc) to give 6-(2,6-diethyl-phenyl)-4-isopropoxy-3-(5-isopropyl-2-methyl-phenoxymethyl)-2-methyl-pyridine 1-oxide. 1H NMR (CDCl3) 7.90 (m, 1H), 7.50-7.04 (m, 3H), 6.90-6.71 (m, 3H), 5.18 (m, 2H), 4.55 (m, 1H), 3.95 (m, 1H), 2.78 (s, 3H), 2.52-2.20 (m, 4H), 2.20 (s, 3H), 1.35 (d, 6H), 1.25 (d, 6H), 1.08 (t, 6H).

Workup

  1. washwashed with saturated Na2CO3, brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified on PTLC (1:1 hexane EtOAc)

Sources & evidence

ORD record
ord-dc3b22f15f0c404a936da111f2ad0595
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

Loading…