1-Tetralone → 2-dimethylaminomethylene-3,4-dihydro-2H-naphthalen-1-one
Reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH3:12][N:13]([CH:15](OC)OC)[CH3:14].CC(OC(N(C)C)N(C)C)(C)C>CC#N>[CH3:12][N:13]([CH:15]=[C:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1]1=[O:11])[CH3:14]Participants
5
Procedure
A solution of 3,4-dihydro-2H-naphthalen-1-one in MeCN and 20 eq. of DMF-DMA were stirred at 90° C. overnight. Thin layer chromatography indicated there is almost no desired product, hence 1.2 equivalents of Bredereck's reagent was added, and the reaction mixture stirred at 80° C. overnight. The solvent was removed under reduced pressure and the crude material was used for the next step with no further purification.
Sources & evidence
- ORD record
- ord-09bf328acb8f40838ce46df9a920fa4f
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700609B2
Reaction notes
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