HCID 90456052, compound → HCID 90456144, compound

HRID 2202103Notes

Reaction equation

HRID 2202103 reaction equation
[OH:1][CH2:2][C:3]1[O:7][CH:6]=[N:5][C:4]=1[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1>ClCCl.O=[Mn]=O>[CH:2]([C:3]1[O:7][CH:6]=[N:5][C:4]=1[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1)=[O:1]

Participants

4

Reactant 1

HCID 90456052HCID 90456052, compound

Product 1

HCID 90456144HCID 90456144, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(5-(hydroxymethyl)oxazol-4-yl)benzonitrile (190 mg, 0.95 mmol, 1.00 equiv) and MnO2 (1.9 g, 21.85 mmol, 23.03 equiv) in dichloromethane (5 mL) was refluxed for 2 h. The reaction mixture was cooled to room temperature and the solid material was removed by filtration. The filtrate was concentrated under vacuum and the residue was purified on a silica gel column eluted with 0-6% of ethyl acetate in petroleum ether to yield 20 mg (11%) of 4-(5-formyloxazol-4-yl)benzonitrile as a white solid. 1H-NMR (300 MHz, CDCl3): δ 10.02 (s, 1H), 8.90 (s, 1H), 8.25 (d, J=8.4 Hz, 1H), 8.08-8.02 (m, 2H) ppm.

Workup

  1. temperaturewas refluxed for 2 h
  2. customthe solid material was removed by filtration
  3. concentrationThe filtrate was concentrated under vacuum
  4. customthe residue was purified on a silica gel column
  5. washeluted with 0-6% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-22473555a63c466786ad200a353fa447
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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