1-{5'-[2-(3,4-Bis(hydroxymethyl)phenyl)ethyl]-2'-methyl-2-propylbiphenyl-4-yl}propan-1-one → 3-(5'-{2-[3,4-Bis(Hydroxymethyl)phenyl]ethyl}-2'-Methyl-2-Propylbiphenyl-4-Yl)pentan-3-Ol
Reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([CH3:32])=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:28])[CH2:26][CH3:27])=[CH:21][C:20]=3[CH2:29][CH2:30][CH3:31])[CH:18]=2)[CH:6]=[CH:7][C:8]=1[CH2:9][OH:10].[CH2:33]([Mg]Br)[CH3:34]>>[CH2:26]([C:25]([C:22]1[CH:23]=[CH:24][C:19]([C:17]2[C:16]([CH3:32])=[CH:15][CH:14]=[C:13]([CH2:12][CH2:11][C:5]3[CH:6]=[CH:7][C:8]([CH2:9][OH:10])=[C:3]([CH2:2][OH:1])[CH:4]=3)[CH:18]=2)=[C:20]([CH2:29][CH2:30][CH3:31])[CH:21]=1)([OH:28])[CH2:33][CH3:34])[CH3:27]Participants
3
Procedure
In a manner similar to that of Example 1(q), by reacting 300 mg (0.7 mmol) of 1-{5′-[2-(3,4-bis(hydroxymethyl)phenyl)ethyl]-2′-methyl-2-propylbiphenyl-4-yl}propan-1-one with 1.9 ml (5.6 mmol) of ethylmagnesium bromide (3M/ether), and after purification on a column of silica eluted with a mixture of heptane and ethyl acetate (40/60), 180 mg (56%) of (4-{2-[4′-(1-ethyl-1-hydroxypropyl)-6-methyl-2′-propylbiphenyl-3-yl]ethyl}-2-hydroxy-methylphenyl)methanol are obtained in the form of white crystals with a melting point of 76° C.
Workup
- customafter purification on a column of silica
- washeluted with a mixture of heptane and ethyl acetate (40/60), 180 mg (56%) of (4-{2-[4′-(1-ethyl-1-hydroxypropyl)-6-methyl-2′-propylbiphenyl-3-yl]ethyl}-2-hydroxy-methylphenyl)methanol
- customare obtained in the form of white crystals with a melting point of 76° C.
Sources & evidence
- ORD record
- ord-eda8e56141a04dfaac51a4d7a0be6a39
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06924400B2
Reaction notes
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