HCID 22615010, compound → HCID 22615065, compound

HRID 843179Notes

Reaction equation

HRID 843179 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]2[C:12]([CH3:17])=[C:13]([CH2:15][OH:16])[O:14][C:10]=2[CH:9]=[CH:8][CH:7]=1>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]2[C:12]([CH3:17])=[C:13]([CH:15]=[O:16])[O:14][C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 22615010HCID 22615010, compound

Product 1

HCID 22615065HCID 22615065, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of [4-(3-bromo-propoxy)-3-methyl-benzofuran-2-yl]methanol (690 mg) in chloroform (10 ml) was added manganese(IV) oxide (1.2 g) at room temperature and the mixture was stirred vigorously overnight. The mixture was filtered through a pad of Celite and concentrated in vacuo. The titled compound (500 mg) was obtained as a white solid after the purification by silica gel column chromatography developed by the mixture of hexane and ethyl acetate. EI-MS: m/z 297 (M+); 1H-NMR (CDCl3): δ 2.38-2.47 (2H, m), 2.74 (3H, s), 3.65 (2H, t, J=6.6 Hz), 4.23 (2H, t, J=5.9 Hz), 6.68 (1H, d, J=7.9 Hz), 7.14 (1H, d, J=8.9 Hz), 7.40 (1H, t, J=8.3 Hz), 9.97 (1H, s).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea59899c963545ddb11fb516120ca9ba
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

Loading…