Triethylamine → Oxime-2,3-dihydro-6-methoxy-1H-inden-1-one

HRID 1750082Notes

Reaction equation

HRID 1750082 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=O)=[CH:5][CH:4]=1.CCN(CC)CC.Cl.[NH2:21][OH:22]>CO>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8]/[C:9]/2=[N:21]\[OH:22])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3340366-Methoxy-1-IndanoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 11389720Oxime-2,3-dihydro-6-methoxy-1H-inden-1-oneYield 93.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 6-methoxy-2,3-dihydro-1H-inden-1-one (6.5 g, 40 mmol) in 100 mL of MeOH was added Et3N (11.1 mL, 80 mmol) and hydroxylamine hydrochloride (3.9 g, 56 mmol). The mixture was stirred at rt for 2 h. The mixture was evaporated and redissolved in EtOAc, the organic phase was washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated to give (E)-6-methoxy-2,3-dihydro-1H-inden-1-one oxime (intermediate 16) (6.6 g, 93%).

Workup

  1. customThe mixture was evaporated
  2. dissolutionredissolved in EtOAc
  3. washthe organic phase was washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ac5b179c0f4c446ba1c1db9d3c4b3b93
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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