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

HRID 1251523Notes

Reaction equation

HRID 1251523 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-e76d530e26544dea94d1cf3093194cf0
Source dataset
uspto-grants-2002_01
Patent number
US06342532B1

Reaction notes

Loading…