Trifluoroacetic acid → HCID 19960963, compound

HRID 1900231Notes

Reaction equation

HRID 1900231 reaction equation
[C:1]([C:3]1[CH2:4][O:5][CH2:6][CH:7]=1)#[N:2].C(N(CC)CC)C.FC(F)(F)C(O)=O.[CH2:22]([N:29]([CH2:35]OC)[CH2:30][Si](C)(C)C)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:22]([N:29]1[CH2:30][C:3]2([C:1]#[N:2])[CH:7]([CH2:6][O:5][CH2:4]2)[CH2:35]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 199609552,5-Dihydrofuran-3-carbonitrile

Product 1

HCID 19960963HCID 19960963, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5.2 g (24.6 mmol, 46% strength) of 3-cyano-2,5-dihydrofuran in 50 ml of absolute methylene chloride is mixed with 0.3 g of triethylamine and 0.3 g of trifluoroacetic acid, the mixture is heated under reflux and then 7 g (29.5 mmol) of N-benzyl-N-methoxymethyl-N-(tri-methylsilylmethyl)-amine are added dropwise. Subsequently, the mixture is heated under reflux for 2 hours and the solution is washed with saturated sodium hydrogen carbonate solution, dried over magnesium sulphate, concentrated and distilled.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux
  3. temperatureSubsequently, the mixture is heated
  4. temperatureunder reflux for 2 hours
  5. washthe solution is washed with saturated sodium hydrogen carbonate solution
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated
  8. distillationdistilled

Sources & evidence

ORD record
ord-5ddab86a852a4e67922bec3495c36c5d
Source dataset
uspto-grants-1996_11
Patent number
US05574161

Reaction notes

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