Hydrochloric Acid → HCID 11066039, compound

HRID 2372103Notes

Reaction equation

HRID 2372103 reaction equation
[CH2:1]([O:8][CH2:9][C:10]#[C:11][CH:12]([OH:17])[C:13]([F:16])([F:15])[F:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](Cl)(=[O:20])[CH3:19].N1C=CC=CC=1.Cl>C(Cl)Cl>[C:18]([O:17][CH:12]([C:11]#[C:10][CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:13]([F:16])([F:15])[F:14])(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 19905844HCID 19905844, compound

Product 1

HCID 11066039HCID 11066039, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a three-necked flask of 50 ml in internal volume which was well dried under reduced pressure in nitrogen stream were charged 20 ml of methylene chloride, 3.57 g (13.0 mmol) of the above alcohol (3) and 1.20 ml (16.9 mmol) of acetyl chloride and then 1.37 ml (16.9 mmol) of pyridine was added thereto under ice-cooling, followed by stirring at room temperature overnight. The reaction was stopped by adding 1N aqueous hydrochloric acid solution and the reaction mixture was extracted with methylene chloride and dried over anhydrous magnesium sulfate. Solvent was distilled off to obtain a crude product, which was purified by silica gel column chromatography to obtain the above acetate (4).

Workup

  1. customIn a three-necked flask of 50 ml in internal volume which was well dried under reduced pressure in nitrogen stream
  2. temperatureunder ice-cooling
  3. extractionthe reaction mixture was extracted with methylene chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationSolvent was distilled off
  6. customto obtain a crude product, which
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-82c37d76652d44c18dd0d18ee968f517
Source dataset
uspto-grants-1992_03
Patent number
US05097075

Reaction notes

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