Trifluoroacetic acid → HCID 12893929, compound

HRID 1156369Notes

Reaction equation

HRID 1156369 reaction equation
[O-:1][C:2]#[N:3].[Na+].FC(F)(F)C(O)=O.[CH3:12][C:13]([C:15]1([CH2:22][OH:23])[CH2:20][CH:19]2[CH2:21][CH:16]1[CH:17]=[CH:18]2)=[O:14]>C(Cl)Cl.O>[CH3:12][C:13]([C:15]1([CH2:22][O:23][C:2](=[O:1])[NH2:3])[CH2:20][CH:19]2[CH2:21][CH:16]1[CH:17]=[CH:18]2)=[O:14]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 517096Sodium CyanateHCID 128937981-[2-(Hydroxymethyl)bicyclo[2.2.1]hept-5-en-2-yl]ethan-1-one

Product 1

HCID 12893929HCID 12893929, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

52 g (0.8 mole) of sodium cyanate, followed dropwise by 95.8 g (0.84 mole) of trifluoroacetic acid, are added to a solution of 66.4 g (0.4 mole) of 2-hydroxymethylnorborn-5-en-2-yl methyl ketone in 120 ml of methylene chloride at 20° C., with slow stirring. The mixture is then stirred for 5 hours at room temperature, after which it is diluted with water. It is then repeatedly extracted with methylene chloride and the organic phases are combined and dried over sodium sulfate. After distilling off the solvent, a crystalline residue (83.1 g=99%) is obtained, and this is recrystallized from ethyl acetate. 45.8 g of 2-carbamyloxymethylnorborn-5-en-2-yl methyl ketone, of melting point 118°-119° C., are obtained.

Workup

  1. extractionIt is then repeatedly extracted with methylene chloride
  2. dry with materialdried over sodium sulfate
  3. distillationAfter distilling off the solvent
  4. customa crystalline residue (83.1 g=99%) is obtained
  5. customthis is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d55f6f0518734c199302d9ccb75a867e
Source dataset
uspto-grants-1982_06
Patent number
US04335138

Reaction notes

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