Aluminium lithium hydride → 4-(3-Ethyl-2-hydroxyphenyl)-4-methyl-2-trifluoromethylpentane-1,2-diol
Reaction equation
C([O:3][C:4](=O)[C:5]([OH:24])([C:20]([F:23])([F:22])[F:21])[CH2:6][C:7]([C:10]1[C:18]2[O:17][CH2:16][CH2:15][C:14]=2[CH:13]=[C:12](Br)[CH:11]=1)([CH3:9])[CH3:8])C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH2:15]([C:14]1[C:18]([OH:17])=[C:10]([C:7]([CH3:9])([CH3:8])[CH2:6][C:5]([C:20]([F:22])([F:23])[F:21])([OH:24])[CH2:4][OH:3])[CH:11]=[CH:12][CH:13]=1)[CH3:16]Participants
3
Procedure
Over-reduction of 10 g (23.51 mmol) of 4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester with lithium aluminum hydride for 14 days at reflux gave 570 mg (7.9%) of 4-(3-ethyl-2-hydroxyphenyl)-4-methyl-2-trifluoromethylpentane-1,2-diol which was methylated by methods analogous to those described in Example 8 and oxidized by methods analogous to those described in Example 1 to afford 4-(3-ethyl-2-methoxyphenyl)-1,1,1-trifluoro-4-methylpentan-2-one. The title compound was prepared by methods analogous to those described in Example 5, using 2-chloro-4-cyanobenzyl bromide.
Sources & evidence
- ORD record
- ord-7814ff8438ff4b3bb79e68f5bd8a773a
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07268152B2
Reaction notes
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