HCID 10207799, compound → HCID 10116312, compound

HRID 840655Notes

Reaction equation

HRID 840655 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:6]([C:8]2[CH:12]=[CH:11][S:10][C:9]=2[C:13]2[CH:14]=[C:15]([CH:19]([OH:24])[C:20]([F:23])([F:22])[F:21])[CH:16]=[N:17][CH:18]=2)[CH:7]=1>ClCCl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[C:6]([C:8]2[CH:12]=[CH:11][S:10][C:9]=2[C:13]2[CH:14]=[C:15]([C:19](=[O:24])[C:20]([F:22])([F:23])[F:21])[CH:16]=[N:17][CH:18]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 10207799HCID 10207799, compound

Product 1

HCID 10116312HCID 10116312, compoundYield 46.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the alcohol of example 4 (0.7 g, 1.5 mmol) in dichloromethane was added manganese dioxide (1.26 g, 14.5 mmol) and the slurry was stirred overnight at room temperature. The reaction mixture was then filtered through a pad of celite and the volatils were evaporated under reduced pressure to give a residue which was purified by flash chromatography (70% CH2Cl2/30% AcOEt) to provide the title compound (0.33 g). 1H nmr (400 MHz, acetone-d6) δ ppm 8.78 (1H, d, J=2.1 Hz), 8.48 (1H, d, J =2.2 Hz), 7.96 (1H, t, J=2.1 Hz), 7.60 (1H, d, J=5.1 Hz), 7.35-7.05 (9H, m), 4.94 (2H, s).

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of celite
  2. customthe volatils were evaporated under reduced pressure
  3. customto give a residue which
  4. customwas purified by flash chromatography (70% CH2Cl2/30% AcOEt)

Sources & evidence

ORD record
ord-efff85b95d6a4ae2a7a588f75fe048e7
Source dataset
uspto-grants-2002_04
Patent number
US06369082B1

Reaction notes

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