Ammonium Chloride → 3-(1,3-Dioxan-2-yl)-1-(4-fluorophenyl)propan-1-one

HRID 1023992Notes

Reaction equation

HRID 1023992 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[CH:4][CH:3]=1.[O:14]1[CH2:19][CH2:18][CH2:17][O:16][CH:15]1[CH2:20][CH2:21][Mg]Br.[NH4+].[Cl-]>C1COCC1>[O:14]1[CH2:19][CH2:18][CH2:17][O:16][CH:15]1[CH2:20][CH2:21][C:6]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:13][CH:12]=1)=[O:7]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 140693474-Fluoro-N-methoxy-N-methylbenzamideHCID 178419673HCID 178419673, compound2×

Product 1

HCID 247278283-(1,3-Dioxan-2-yl)-1-(4-fluorophenyl)propan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 4-fluoro-N-methoxy-N-methylbenzamide (0.94 mmol; 173 mg) in anhydrous THF (2 mL), at −78° C. under argon, was added a solution of (1,3-dioxan-2-ylethyl)magnesium bromide, 0.5M in THF (1.04 mmol; 2.1 mL). The reaction was stirred 16 hours at room temperature. The mixture was cooled to −78° C. and (1,3-dioxan-2-ylethyl)magnesium bromide, 0.5M in THF (2.00 mmol; 4 mL) was added again. The reaction was stirred overnight at room temperature. The mixture was treated with saturated NH4Cl and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, and concentrated in vacuo. The title compound was prepared in quantitative yield, used without further purification.

Workup

  1. temperatureThe mixture was cooled to −78° C.
  2. stirringThe reaction was stirred overnight at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customused without further purification

Sources & evidence

ORD record
ord-152ed29a94b84454a09037342580b2bb
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

Loading…