Diethylamine → 6-Hydroxy-3-methyl-4-trifluoromethanesulfonyloxy-phthalic Acid Dimethyl Ester
Reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[C:5](=[C:10]([CH3:26])[C:11]([O:18][S:19]([C:22]([F:25])([F:24])[F:23])(=[O:21])=[O:20])=[CH:12][C:13]=1[O:14]CC=C)[C:6]([O:8][CH3:9])=[O:7].C(NCC)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:27])[C:4]1[C:5](=[C:10]([CH3:26])[C:11]([O:18][S:19]([C:22]([F:23])([F:25])[F:24])(=[O:21])=[O:20])=[CH:12][C:13]=1[OH:14])[C:6]([O:8][CH3:9])=[O:7]Participants
Procedure
To a solution of 6-allyloxy-3-methyl-4-trifluoromethanesulfonyloxy-phthalic acid dimethyl ester (8.39 g, 20.3 mmol) in toluene (20 mL) was added tetrakistriphenylphosphine palladium (0.47 g, 0.40 mmol) and diethylamine (2.97 g, 40.86 mmol) at room temperature under an atmosphere of nitrogen. Stirring at room temperature was continued until all starting material was consumed. The crude reaction mixture was partitioned between diethyl ether and HCl (0.1 N). The organic layer was washed with brine and dried over sodium sulfate. Filtration and evaporation of solvents in vacuo yielded a crude material, which was purified by silica gel chromatography to provide 4.16 g (55%) of the desired product as an off-white solid. NMR (300 MHz, CDCl3): δ=2.20 (s, 3H), 3.93 (s, 3H), 3.95 (s, 3H), 7.01 (s, 1H) ppm; 19F NMR (282 MHz, CDCl3): δ=−74 ppm.
Workup
- customwas consumed
- customThe crude reaction mixture
- customwas partitioned between diethyl ether and HCl (0.1 N)
- washThe organic layer was washed with brine
- dry with materialdried over sodium sulfate
- filtrationFiltration and evaporation of solvents in vacuo
- customyielded a crude material, which
- customwas purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-bccd789039364fa699c639e9b022d5d1
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871785B2
Reaction notes
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