HCID 59599684, compound → HCID 59599685, compound

HRID 2266641Notes

Reaction equation

HRID 2266641 reaction equation
[F:1][C:2]1[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[N:4][C:3]=1[CH2:15][OH:16]>ClCCl.O=[Mn]=O>[F:1][C:2]1[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=[N:4][C:3]=1[CH:15]=[O:16]

Participants

4

Reactant 1

HCID 59599684HCID 59599684, compound

Product 1

HCID 59599685HCID 59599685, compoundYield 77.9%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [5-fluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-yl]-methanol (339 mg) at room temperature in dichloromethane (15 ml) under an argon atmosphere was added MnO2 (1.20 g). The black suspension was heated to reflux and stirring at that temperature was continued for 18 hours, then was cooled to room temperature and filtered. The resulting cake was washed with dichloromethane. The filtrate was concentrated to leave 5-fluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbaldehyde (262 mg) as light yellow viscous oil. The crude product was used in the next reaction step without further purification. MS (EI): 171.1 ([M-Si(Me)3]).

Workup

  1. temperatureThe black suspension was heated
  2. temperatureto reflux
  3. filtrationfiltered
  4. washThe resulting cake was washed with dichloromethane
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-77b6e369f82246c39c2f0c46b8f16eaa
Source dataset
uspto-grants-2010_12
Patent number
US07858652B2

Reaction notes

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