[5-(3-[1,3]Dioxan-2-yl-phenylsulfanyl)-4-fluoro-2-nitro-phenyl]-methanol → 5-(3-[1,3]Dioxan-2-yl-phenylsulfanyl)-4-fluoro-2-nitro-benzaldehyde

HRID 658067Notes

Reaction equation

HRID 658067 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[C:9]([S:13][C:14]2[C:15]([F:25])=[CH:16][C:17]([N+:22]([O-:24])=[O:23])=[C:18]([CH2:20][OH:21])[CH:19]=2)[CH:10]=[CH:11][CH:12]=1>C(Cl)(Cl)Cl.O=[Mn]=O>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[C:9]([S:13][C:14]2[C:15]([F:25])=[CH:16][C:17]([N+:22]([O-:24])=[O:23])=[C:18]([CH:19]=2)[CH:20]=[O:21])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 86634266[5-(3-[1,3]Dioxan-2-yl-phenylsulfanyl)-4-fluoro-2-nitro-phenyl]-methanol

Product 1

HCID 866342675-(3-[1,3]Dioxan-2-yl-phenylsulfanyl)-4-fluoro-2-nitro-benzaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

[5-(3-[1,3]Dioxan-2-yl-phenylsulfanyl)-4-fluoro-2-nitro-phenyl]-methanol (2.22 g, 6.08 mmol) was placed in chloroform (250 mL), and MnO2 (6.4 g) was added. The resulting mixture was stirred overnight at room temperature. After 18 h of stirring, the mixture was heated at 40° C. for 1 hour. The resulting mixture was worked up by filtration through Celite®. The filtrate was concentrated to yield an oil, which was purified by silica column chromatography (20% EtOAc/heptane) to yield a solid.

Workup

  1. stirringAfter 18 h of stirring
  2. temperaturethe mixture was heated at 40° C. for 1 hour
  3. filtrationThe resulting mixture was worked up by filtration through Celite®
  4. concentrationThe filtrate was concentrated
  5. customto yield an oil, which
  6. customwas purified by silica column chromatography (20% EtOAc/heptane)
  7. customto yield a solid

Sources & evidence

ORD record
ord-d128fd08dcc24b1ba012e7cced914889
Source dataset
uspto-grants-2011_12
Patent number
US08076358B2

Reaction notes

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