3-Methyl-4-anisaldehyde → 1-Phenyl-1-propanol

HRID 50047

Reaction equation

HRID 50047 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]=1

Participants

3

Reactant 2

HCID 1229363-Methyl-4-anisaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 71471-Phenyl-1-propanol

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

Linked notes

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