Triethylamine → 4H-1-Benzopyran-4-one, 2,3-dihydro-, oxime

HRID 2382676Notes

Reaction equation

HRID 2382676 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[CH2:3][CH2:2]1.C(N(CC)CC)C.Cl.[NH2:20][OH:21]>CO.C(OCC)(=O)C>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[N:20][OH:21])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 68110ChromanoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 44866984H-1-Benzopyran-4-one, 2,3-dihydro-, oximeYield 146%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chromanone (10 g, 67.6 mmol) in methanol (150 mL) was added triethylamine (15 mL, 108.1 mmol) and hydroxylamine hydrochloride (7.5 g, 108.1 mmol). The mixture was stirred at rt for 16 hrs. The solvent was evaporated giving a residue which was dissolved in ethyl acetate and extracted with water. The organic layer was separated and dried over anhydrous sodium sulfate. Evaporation of the filtrate afforded chroman-4-one oxime (16.1 g, 100%) as a white crystalline solid. MS: 164.0 (M+H)+; tR=1.99 min (method 1).

Workup

  1. customThe solvent was evaporated
  2. customgiving a residue which
  3. extractionextracted with water
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-6967bcc475c448658b432b68849acd2e
Source dataset
uspto-grants-2012_09
Patent number
US08263588B2

Reaction notes

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