Potassium Carbonate → 2-Tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-7-(2-methylprop-1-enyl)naphthalen-2-yl)acetic acid
Reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:30])[C:8]([CH:19]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])C(OCC)=O)=[C:9]2[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[CH3:31][C:32]1([CH3:43])[C:36](C)(C)OB(C=C(C)C)O1.[C:44]([O-:47])([O-])=[O:45].[K+].[K+].CC#N.O>C1(C)C=CC=CC=1.C(O)C.O>[C:26]([O:25][CH:19]([C:8]1[C:7]([CH3:30])=[CH:6][C:5]2[C:10](=[CH:11][C:2]([CH:31]=[C:32]([CH3:43])[CH3:36])=[CH:3][CH:4]=2)[C:9]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[C:44]([OH:47])=[O:45])([CH3:27])([CH3:28])[CH3:29]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
2-tert-Butoxy-2-(1-(4-chlorophenyl)-3-methyl-7-(2-methylprop-1-enyl)naphthalen-2-yl)acetic acid (77) was prepared by the method of Example 67 from ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate using 4,4,5,5-tetramethyl-2-(2-methylprop-1-enyl)-1,3,2-dioxaborolane and K2CO3 instead of triethylamine, and toluene, ethanol, water as a solvent mixture. 1H-NMR: 400 MHz, (CD3OD) δ: 7.69 (d, J=8 Hz, 1H), 7.61 (s, 1H), 7.54 (m, 3H), 7.27 (m, 2H), 7.02 (s, 1H), 6.23 (s, 1H), 5.18 (s, 1H), 2.57 (s, 3H), 1.83 (s, 3H), 1.68 (s, 3H), 0.97 (s, 9H). HPLC (Kinetex 2.6u, 50×4.6 mm, 2-100% MeCN/H2O+0.05% HOAc, 5 min run): tR (min)=3.98.
Sources & evidence
- ORD record
- ord-4b5132b8d1f64f419455376fa3adad2a
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102614B2
Reaction notes
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