[5-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)phenyl]phenylmethanol → [5-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)phenyl]phenylmethanone

HRID 2075958Notes

Reaction equation

HRID 2075958 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([O:29][CH3:30])=[CH:11][C:12]([C:23]2[N:27]=[C:26]([CH3:28])[O:25][N:24]=2)=[C:13]([CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[OH:16])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[O-2].[O-2].[Mn+4].C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:10]([O:29][CH3:30])=[CH:11][C:12]([C:23]2[N:27]=[C:26]([CH3:28])[O:25][N:24]=2)=[C:13]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 59565729[5-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)phenyl]phenylmethanol

Product 1

HCID 50899156[5-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)phenyl]phenylmethanoneYield 100.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst3×HCID 6344DichloromethaneSolvent

Procedure

A mixture of [5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl]phenyl)phenylmethanol (reference example 6-1) (526 mg), manganese dioxide (1.18 g) and methylene chloride (6.8 mL) was stirred at room temperature overnight. After addition of manganese dioxide (1.18 g), the mixture was stirred for 7.5 hours, and manganese dioxide (0.59 g) was added, and the mixture was stirred overnight. The mixture was passed through a layer of Celite (registered mark). The filtrate was concentrated under reduced pressure to give the title compound (526 mg).

Workup

  1. stirringthe mixture was stirred for 7.5 hours
  2. stirringthe mixture was stirred overnight
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-03d3ef33e3fa4547a5136e6c548a0bfc
Source dataset
uspto-grants-2011_04
Patent number
US07923462B2

Reaction notes

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