Triethylamine → Oxime-2,3-dihydro-6-methoxy-1H-inden-1-one
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- customThe mixture was evaporated
- dissolutionredissolved in EtOAc
- washthe organic phase was washed with water, brine
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ac5b179c0f4c446ba1c1db9d3c4b3b93
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156822B2
Reaction notes
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