Ammonium Chloride → Acetone O-[5-methoxy-2-(6-methoxy-2-naphthoyl)phenyl]oxime

HRID 1061850Notes

Reaction equation

HRID 1061850 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8](=[N:10][OH:11])[CH3:9].F[C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[C:21]([C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28]([O:33][CH3:34])[CH:29]=2)[CH:24]=1)=[O:22].[Cl-].[NH4+]>C1COCC1>[CH3:20][O:19][C:17]1[CH:16]=[CH:15][C:14]([C:21]([C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[C:28]([O:33][CH3:34])[CH:29]=3)[CH:24]=2)=[O:22])=[C:13]([O:11][N:10]=[C:8]([CH3:9])[CH3:7])[CH:18]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 67180Acetone, oximeHCID 22285703(2-Fluoro-4-methoxyphenyl)(6-methoxy-2-naphthyl)methanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 11451339Acetone O-[5-methoxy-2-(6-methoxy-2-naphthoyl)phenyl]oximeYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium tert-butoxide (1.2 g, 10.6 mmol) was added into a solution of acetone oxime (0.78 g, 10.6 mmol) and THF (15 mL). After stirring for 1 h, (2-fluoro-4-methoxyphenyl)(6-methoxy-2-naphthyl)methanone (3.0 g, 9.7 mmol) in THF (3 mL) was added. The reaction mixture was refluxed for 3 h, then cooled to room temperature, poured into aqueous ammonium chloride, and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (hexanes/EtOAc 3/1) gave a brown solid (3.35 g, 95% yield, m.p. 117-118° C.); MS m/e 364 (M+).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried over MgSO4
  4. customEvaporation and purification by flash chromatography (hexanes/EtOAc 3/1)

Sources & evidence

ORD record
ord-a94c27bc4fce4a5093f6de465917248d
Source dataset
uspto-grants-2005_11
Patent number
US06960607B2

Reaction notes

Loading…