O-Methylhydroxylamine hydrochloride → 7-tert-Butyl-chroman-4-one O-methyl-oxime

HRID 1158786Notes

Reaction equation

HRID 1158786 reaction equation
[C:1]([C:5]1[CH:14]=[C:13]2[C:8]([C:9](=O)[CH2:10][CH2:11][O:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:17][O:18][NH2:19]>N1C=CC=CC=1>[CH3:17][O:18][N:19]=[C:9]1[C:8]2[C:13](=[CH:14][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=2)[O:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 595485417-(Tert-butyl)chroman-4-one

Product 1

HCID 866054407-tert-Butyl-chroman-4-one O-methyl-oximeYield 89.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The product of Example 1A (1.50 g, 7.3 mmol) and methoxyamine hydrochloride (0.69 g, 8 mmol) were dissolved in 7 mL of pyridine. The reaction mixture was stirred at ambient temperature for 16 hours, and the pyridine removed under reduced pressure. The residue was taken in diethyl ether and sequentially washed with water and 1N aqueous hydrochloric acid. The isolated organic layer was then dried with magnesium sulfate, filtered and the solvent removed under reduced pressure to give 1.53 g of the title compound, which was used without further purification. MS (DCI) m/e 234 (M+H)+

Workup

  1. customthe pyridine removed under reduced pressure
  2. washsequentially washed with water and 1N aqueous hydrochloric acid
  3. dry with materialThe isolated organic layer was then dried with magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-1c1b7fd9694d41e3a9710eda0df83f08
Source dataset
uspto-grants-2010_10
Patent number
US07812019B2

Reaction notes

Loading…