Lithium Hydroxide → (+/-)-2-Methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoic acid
Reaction equation
[CH3:1][C:2]([S:25]([CH3:28])(=[O:27])=[O:26])([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([B:16]2[O:20][C:19]([CH3:22])([CH3:21])[C:18]([CH3:24])([CH3:23])[O:17]2)=[CH:12][CH:11]=1)[C:3]([O:5]CC)=[O:4].[OH-].[Li+].BrC1C=CC(CCC(C)(S(C)(=O)=O)C(O)=O)=CC=1>>[CH3:1][C:2]([S:25]([CH3:28])(=[O:26])=[O:27])([CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([B:16]2[O:20][C:19]([CH3:21])([CH3:22])[C:18]([CH3:23])([CH3:24])[O:17]2)=[CH:14][CH:15]=1)[C:3]([OH:5])=[O:4]Participants
4
Reactant 3
Product 1
Procedure
The title compound (5.47 g, 100%) was prepared from (+/−)-ethyl 2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoate (5.2 g, 12.7 mmol) and lithium hydroxide (2.13 g, 50.8 mmol) by a procedure analogous to that described for (+/−)-4-(4-bromophenyl)-2-methyl-2-(methylsulfonyl)butanoic acid (II/Step 3-Preparation Number 2). LCMS m/z 381.6 (M−1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.36 (s, 12H) 1.75 (s, 3H) 2.19-2.30 (m, 1H) 2.44-2.55 (m, 1H) 2.56-2.67 (m, 1H) 2.76-2.87 (m, 1H) 3.09 (s, 3H) 7.23 (d, J=8.01 Hz, 2H) 7.76 (d, J=8.20 Hz, 2H).
Sources & evidence
- ORD record
- ord-1dbd28fc525543eeab3149e0c28db235
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853258B2
Reaction notes
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