Water → HCID 86628626, compound

HRID 657545Notes

Reaction equation

HRID 657545 reaction equation
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].O[C:17]1[CH:18]=[C:19]2[C:22](=[CH:23][CH:24]=1)[CH:21]([C:25]#[N:26])[CH2:20]2.C(N(CC)CC)C.O>ClCCl>[F:5][C:4]([F:7])([F:6])[S:1]([O:8][C:17]1[CH:18]=[C:19]2[C:22](=[CH:23][CH:24]=1)[CH:21]([C:25]#[N:26])[CH2:20]2)(=[O:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 12159643HCID 12159643, compound

Product 1

HCID 86628626HCID 86628626, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.4 mL of triflic anhydride (1.2 equivalents) are poured at 0° C., over 1 hour, into a solution of 2 g (13.8 mmoles) of 3-hydroxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile in 40 mL of dichloromethane and 3.9 mL (2 equivalents) of triethylamine. Stirring is carried out for 3 days at 25° C. The reaction mixture is poured into water, extracted with dichloromethane, dried over MgSO4, filtered and evaporated to obtain 3.8 g of an oil. This residue is purified by flash chromatography over 150 g of silica; eluant=100% toluene. The expected product is obtained in the form of an oil.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-45229766a8e94a15b2e53d4457a79817
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

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