Tetrabutylammonium Fluoride Trihydrate → HCID 67884017, compound

HRID 1613599Notes

Reaction equation

HRID 1613599 reaction equation
O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:22]1[CH:29]2[CH:23]1[CH2:24][CH2:25][O:26][C:27]1[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=12.[Cl:34][C:35]1[CH:36]=[CH:37][C:38]([O:41][Si](C)(C)C)=[N:39][CH:40]=1>O>[Cl:34][C:35]1[CH:36]=[CH:37][C:38](=[O:41])[N:39]([C@@H:29]2[C:28]3[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=3[O:26][CH2:25][CH2:24][C@H:23]2[OH:22])[CH:40]=1

Participants

5

Reactant 3

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 13149080HCID 13149080, compoundHCID 14517467HCID 14517467, compound

Product 1

HCID 67884017HCID 67884017, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

22.7 g (72 mmol) of tetrabutylammonium fluoride trihydrate are added to a mixture of 10.54 g (65 mmol) of 4,5-epoxy-2,3,4,5-tetrahydro-1-benzoxepin and 19.4 g (96 mmol) of 5-chloro-2-trimethylsilyloxy-pyridine, and the mixture is heated at 90° C. for 3 hours. The mixture is stirred into water and extracted several times with ethyl acetate. The combined organic phases are washed with water and saturated sodium chloride solution, and the solvent is evaporated off in vacuo. The residue is crystallized in n-butyl acetate. Crystals of melting point 175.5°-177.5° C. are obtained.

Workup

  1. extractionextracted several times with ethyl acetate
  2. washThe combined organic phases are washed with water and saturated sodium chloride solution
  3. customthe solvent is evaporated off in vacuo
  4. customThe residue is crystallized in n-butyl acetate
  5. customCrystals of melting point 175.5°-177.5° C. are obtained

Sources & evidence

ORD record
ord-3cad651ae9ba4f6ab02a8b651151dfe6
Source dataset
uspto-grants-1993_03
Patent number
US05194442

Reaction notes

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