Water → 2-Methyl-7-(2-thienyl)-1-indanone
Reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[CH:8]([CH3:12])[CH2:7]2.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>C(COC)OC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1C1C=CC=CC=1P(C1C=CC=CC=1C1C=CC=CC=1C)C1C=CC=CC=1C1C=CC=CC=1C>[CH3:12][CH:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:14]3[S:13][CH:17]=[CH:16][CH:15]=3)[CH:3]=[CH:4][CH:5]=2)[C:9]1=[O:11]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
Using a method similar to Example 15a), 11.25 g (0.05 mol) of (2), 13.4 g (0.055 mol) of thiophenylboronic acid and 11.7 g (0.11 mol) of sodium carbonate were placed in 190 ml of dimethoxyethane and 60 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. 225 mg (1 mmol) of palladium acetate and 0.609 g (2 mmol) of tris(o-tolylphenyl)phosphine were added and the reaction mixture was stirred for 2 hours at 80° C. After addition of 150 ml of water, the mixture was extracted 4 times with 100 ml each time of diethyl ether, the ether phase was washed twice with 50 ml each time of water and dried over magnesium sulfate. Removal of the solvent gave 8.6 g of (22) as an oil.
Workup
- custom60 ml of water in the reaction vessel, the mixture was degassed a number of times
- extractionthe mixture was extracted 4 times with 100 ml each time of diethyl ether
- washthe ether phase was washed twice with 50 ml each time of water
- dry with materialdried over magnesium sulfate
- customRemoval of the solvent
Sources & evidence
- ORD record
- ord-60a25d30274e480db4cecc021b6d2ce6
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06492539B1
Reaction notes
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