3-Methyl-4-anisaldehyde → 1-Phenyl-1-propanol
Reaction equation
C[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1OC)[CH:5]=[O:6].[CH2:12]([Mg]Br)[CH3:13]>>[CH3:12][CH2:13][CH:5]([OH:6])[C:4]1[CH:7]=[CH:8][CH:9]=[CH:2][CH:3]=1Participants
3
Procedure
The synthesis of the title compound (26F) was accomplished in a four-step, three-pot reaction sequence. Commercially available 3-methyl-p-anisaldehyde was reacted with ethylmagnesium bromide to provide its phenylpropanol derivative. This alcohol was then oxidized to the corresponding ketone in the usual manner with PCC. This ketone was subsequently reacted with (R)-naphthyl-1-ethylamine in the presence of Ti(i-PrO)4 to provide the imine. This imine was reduced in high diastereoselective yield by catalytic hydrogenation in the presence of Raney-nickel.
Sources & evidence
- ORD record
- ord-5b000c4f46ae49fe8920d7c9a15505cf
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06710088B2
Reaction notes
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