18-Crown-6 → HCID 57551951, compound

HRID 218085Notes

Reaction equation

HRID 218085 reaction equation
[F-:1].[K+].[CH2:3]1OCCOCCOCCOCCOCCOC1.Br[CH2:22][C:23]([C:25]1[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=1)=[O:24]>C(#N)C.O>[CH3:3][O:31][C:29](=[O:30])[C:28]1[CH:32]=[CH:33][C:25]([C:23](=[O:24])[CH2:22][F:1])=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 27568364-(2-bromoacetyl)benzoic Acid

Product 1

HCID 57551951HCID 57551951, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of potassium fluoride (3.11 mmol) in acetonitrile (1 mL) was added 18-crown-6 (0.1 mmol) and the reaction was heated at 90° C. for 30 mins. 4-(2-Bromo-acetyl)-benzoic acid (1.56 mmol) was added and the reaction heated at 90° C. for 16 h. The reaction was diluted with water (10 mL) and extracted with ethyl acetate (3×20 mL). The product was purified on silica eluting with 5-15% ethyl acetate in iso-hexane to yield on concentration in vacuo of the desired fractions, the title product as a white solid (31%). 1H NMR (400 MHz, CDCl3) 3.98 (3H, s), 5.55 (2H, d, J=50 Hz), 7.95 (2H, d, J=8 Hz), 8.18 (2H, d, J=8 Hz).

Workup

  1. temperaturethe reaction heated at 90° C. for 16 h
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. customThe product was purified on silica eluting with 5-15% ethyl acetate in iso-hexane
  4. customto yield on concentration in vacuo of the desired fractions

Sources & evidence

ORD record
ord-c9ece823c18e49ddb220b41aff65a3d8
Source dataset
uspto-grants-2012_06
Patent number
US08198283B2

Reaction notes

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