Ammonium fluoride → HCID 25017344, compound

HRID 511974Notes

Reaction equation

HRID 511974 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][S:22](Cl)(=[O:24])=[O:23])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[F-:27]>CC(C)=O.C(OCC)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][S:22]([F:27])(=[O:24])=[O:23])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 25516Ammonium fluorideHCID 25017079HCID 25017079, compound

Product 1

HCID 25017344HCID 25017344, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 12.1 (0.345 g, 0.9 mmol) in dry acetone (20 mL), was added anhydrous NH4F (0.066 g, 1.8 mmol) and the mixture refluxed for 2 hours. The reaction mixture was cooled to room temperature, the solvent was evaporated, and the residue obtained was dissolved in diethyl ether (20 mL). The ethereal solution was successively washed with water and brine, dried (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography on silica gel (20% diethyl ether-hexane) afforded 13.1 (0.306 g, 93% yield) as a white solid (m p 35-38° C.).

Workup

  1. temperaturethe mixture refluxed for 2 hours
  2. customthe solvent was evaporated
  3. customthe residue obtained
  4. washThe ethereal solution was successively washed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash column chromatography on silica gel (20% diethyl ether-hexane)

Sources & evidence

ORD record
ord-708b72d651a5443fbc175c7568cc383a
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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