HCID 66993841, compound → HCID 59678263, compound

HRID 1392662Notes

Reaction equation

HRID 1392662 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]([CH:18]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:23][CH2:22][CH:21]=2)[OH:19])=[C:13]([O:30][CH3:31])[CH:12]=1)[CH3:2]>ClCCl.[O-2].[O-2].[Mn+4]>[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]([C:18]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=1)[CH3:2]

Participants

4

Reactant 1

HCID 66993841HCID 66993841, compound

Product 1

HCID 59678263HCID 59678263, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese dioxide (390 mg, 4.5 mmol) is added to a solution of [6-(2,6-diethyl-phenyl)-4-methoxy-2-methyl-pyridin-3-yl]-(3,4-dihydro-naphthalen-1-yl)-methanol (63 mg, 0.15 mmol) in dichloromethane (10 mL). The mixture is stirred overnight at room temperature. The mixture is filtered on celite and the filtrate concentrated and chromatographed on silica gel to give [6-(2,6-diethyl-phenyl)-4-methoxy-2-methyl-pyridin-3-yl]-naphthalen-1-yl-methanone. 1H NMR (CDCl3) 9.22 (d, 1H), 8.09 (d, 1H), 7.95 (d, 1H), 7.74 (t, 2H), 7.62 (t, 1H), 7.50 (t, 1H), 7.32 (t, 1H), 7.18 (d, 2H), 6.77 (s, 1H), 3.69 (s, 3H), 2.50-2.42 (m, 4H), 2.47 (s, 3H), 1.14 (t, 6H).

Workup

  1. filtrationThe mixture is filtered on celite
  2. concentrationthe filtrate concentrated
  3. customchromatographed on silica gel

Sources & evidence

ORD record
ord-c38cf9ff85ac4b2c97380be500cc3aaa
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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