HCID 69080912, compound → HCID 86695610, compound

HRID 594224Notes

Reaction equation

HRID 594224 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][OH:15])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=1>C1COCC1.O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=1)[CH:14]=[O:15]

Participants

4

Reactant 1

HCID 69080912HCID 69080912, compound

Product 1

HCID 86695610HCID 86695610, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3-chloro-5-(pyridin-2-yl)phenyl)methanol (116 mg; 0.64 mmol) in anh. THF (6 ml) was treated with MnO2 (877 mg; 10.09 mmol), and the resulting mixture was stirred at rt, under nitrogen, for 6.5 h. The resulting reaction mixture was then filtered over celite, and the separated solids were washed with THF. The filtrate was concentrated to dryness under reduced pressure giving 3-chloro-5-(pyridin-2-yl)benzaldehyde as a yellow oil. LC-MS (conditions A): tR=0.43 min.; no ionisation.

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas then filtered over celite
  3. washthe separated solids were washed with THF
  4. concentrationThe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-63c513023cfe4f24a8cf2216d1f13ac0
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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