(3-Cyclopentyloxy-4-methoxyphenyl)(2-furyl)methanol → (3-Cyclopentyloxy-4-methoxyphenyl)-(2-furyl)ketone

HRID 1079415Notes

Reaction equation

HRID 1079415 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([C:17]3[O:18][CH:19]=[CH:20][CH:21]=3)[OH:16])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]([C:17]3[O:18][CH:19]=[CH:20][CH:21]=3)=[O:16])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 19959391(3-Cyclopentyloxy-4-methoxyphenyl)(2-furyl)methanol

Product 1

HCID 19959406(3-Cyclopentyloxy-4-methoxyphenyl)-(2-furyl)ketoneYield 59.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

The alcohol (3.2 g) was stirred with manganese (IV) oxide (10 g) in CH2Cl2 (100 ml) at RT for 3 h. The mixture was filtered through Celite® and the filtrate concentrated in vacuo. The residual dark oil was subjected to chromatography (SiO2) to give (3-cyclopentyloxy-4-methoxyphenyl)-(2-furyl)ketone (1.9 g); νmax (neat) 1620 cm-1.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-a284ae3d7018462ab5de879d577cc04f
Source dataset
uspto-grants-1996_12
Patent number
US05580888

Reaction notes

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