HCID 90203660, compound → HCID 90203267, compound

HRID 927047Notes

Reaction equation

HRID 927047 reaction equation
[CH3:1][S:2]([C:5]1[CH:20]=[CH:19][C:8]([CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][OH:18])=[N:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([CH:17]=[O:18])=[N:15][CH:16]=2)=[CH:19][CH:20]=1)(=[O:4])=[O:3]

Participants

4

Reactant 1

HCID 90203660HCID 90203660, compound

Product 1

HCID 90203267HCID 90203267, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Manganese dioxide (14.0 g, 161 mmol) was added to a solution of [5-(4-methanesulfonyl-benzyloxy)-pyridin-2-yl]-methanol (4.04 g, 13.77 mmol) in chloroform. The resulting mixture was heated to 60° C. for 10 min after which it was filtered through Celite and the filtrate washed with CH2Cl2. Volatiles were removed under reduced pressure. The crude mixture was dry-loaded onto silica gel and 5-(4-methanesulfonyl-benzyloxy)-pyridine-2-carbaldehyde (2.44 g, 61%) was isolated by chromatography (60% ethyl acetate in hexane).

Workup

  1. filtrationwas filtered through Celite
  2. washthe filtrate washed with CH2Cl2
  3. customVolatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-aa78bdf1242448bc963c8ed8f39141a3
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

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