Ammonium Chloride → HCID 57827301, compound

HRID 1693208Notes

Reaction equation

HRID 1693208 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15]#[N:16].[CH2:17]([O:20][CH2:21][CH2:22]OS(C1C=CC(C)=CC=1)(=O)=O)[CH:18]=[CH2:19].C1OCCOCCOCCOCCOCCOC1.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[CH2:17]([O:20][CH2:21][CH2:22][CH:14]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[F:7])[C:15]#[N:16])[CH:18]=[CH2:19]

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 2855718-Crown-6HCID 67592Benzeneacetonitrile, 2-fluoro-HCID 13459385HCID 13459385, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 57827301HCID 57827301, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium tert-butoxide (9.93 g) was added to a solution of 2-fluorophenylacetonitrile (10 g), toluene-4-sulfonic acid 2-allyloxyethyl ester (19 g) and 18-crown-6 (3.91 g) in tetrahydrofuran (400 mL) under ice-cooling. The reaction solution was stirred at the same temperature for 10 minutes. The reaction solution was warmed to room temperature and further stirred for four hours. Aqueous ammonium chloride and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (10.9 g).

Workup

  1. temperaturecooling
  2. stirringfurther stirred for four hours
  3. customthe organic layer was separated
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-576f8524a38d4d8eb9a0d36fee68ed8f
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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