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Potassium Carbonate → 2,2-dimethyl-5-fluoromethyl-5-[2-(2-nitro-1H-imidazol-1-yl)ethyl]-1,3-dioxane

HRID 514640
Notes
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Reaction equation

HRID 514640 reaction equation
[CH3:1][C:2]1([CH3:30])[O:7][CH2:6][C:5]([CH2:20][CH2:21][N:22]2[CH:26]=[CH:25][N:24]=[C:23]2[N+:27]([O-:29])=[O:28])([CH2:8]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:4][O:3]1.C1N2CCOCCOCCN(CCOCCOCC2)CCOCCOC1.[F-:57].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH3:1][C:2]1([CH3:30])[O:7][CH2:6][C:5]([CH2:8][F:57])([CH2:20][CH2:21][N:22]2[CH:26]=[CH:25][N:24]=[C:23]2[N+:27]([O-:29])=[O:28])[CH2:4][O:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 728012,2,2-CryptandHCID 522689Potassium FluorideHCID 90300383HCID 90300383, compound

Product 1

HCID 894723032,2-dimethyl-5-fluoromethyl-5-[2-(2-nitro-1H-imidazol-1-yl)ethyl]-1,3-dioxane

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6342AcetonitrileSolvent

Procedure

5 mg (11.4 μmol equivalents) of 2,2-dimethyl-5-[2-(2-nitro-1H-imidazol-1-yl)ethyl]-5-(p-toluenesulfonyloxymethyl)-1,3-dioxane was dissolved in 1 mL of acetonitrile, 14 mg (34.5 μmol equivalents) of Kryptofix 222 (trade name, Merck), 0.82 g (14.1 μmol equivalents) of potassium fluoride, and 0.4 mg (2.9 μmol equivalents) of potassium carbonate were added thereto, and the mixture was refluxed while heating for 5 hours. After completion of the reaction, water was added and the mixture was extracted three times with chloroform. The combined chloroform layers were dried with anhydrous magnesium sulfate and subsequently concentrated under vacuum. The obtained crude product was purified by silica gel column chromatography to give a trace amount of 2,2-dimethyl-5-fluoromethyl-5-[2-(2-nitro-1H-imidazol-1-yl)ethyl]-1,3-dioxane.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewhile heating for 5 hours
  3. additionwas added
  4. extractionthe mixture was extracted three times with chloroform
  5. dry with materialThe combined chloroform layers were dried with anhydrous magnesium sulfate
  6. concentrationsubsequently concentrated under vacuum
  7. customThe obtained crude product
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-580166d362e24caeb0a8f552f095afce
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09107964B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes