Methyl Acrylate → Methyl trans-3-[4-(pentafluorosulfanyl)phenyl]prop-2-enoate
Reaction equation
F[B-](F)(F)F.[F:6][S:7]([F:19])([F:18])([F:17])([F:16])[C:8]1[CH:13]=[CH:12][C:11]([N+]#N)=[CH:10][CH:9]=1.[C:20]([O:24][CH3:25])(=[O:23])[CH:21]=[CH2:22]>C(O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:6][S:7]([F:19])([F:18])([F:17])([F:16])[C:8]1[CH:13]=[CH:12][C:11](/[CH:22]=[CH:21]/[C:20]([O:24][CH3:25])=[O:23])=[CH:10][CH:9]=1Participants
Procedure
(Bowden, et al., Tetrahedron 2000, 56, 3393-3408) Palladium(II) acetate (0.5 mg, 0.002 mmol) was added to a solution of 1 (10.9 mg, 0.0343 mmol) and methyl acrylate (15.6 mg, 0.181 mmol) in 0.18 g of 95% aqueous ethanol. The reaction mixture as stirred at room temperature for 18 h, filtered through a pad of Celite 545 with CH2Cl2, and purified by SiO2 column chromatography (6:4 hexane/CH2Cl2) to give 3 (8.4 mg, 85% yield) as colorless crystals; m.p. 80.5-81.5° C. MS (GC, EI): m/z=288 [M+], 269 [M+-F], 257, 130, 102. IR (ATR): {tilde over (v)}=1701, 1640, 1439, 1317, 1213, 1101, 999, 845, 816 cm−1. 1H NMR (500 MHz, CDCl3): δ=7.78 (d, J=8.7 Hz, 2H), 7.68 (d, J=16.1 Hz, 1H), 7.60 (d, J=8.7 Hz, 2H), 7.61 (d, J=16.1 Hz, 1H), 3.83 (s, 3H) ppm. 13C NMR (125 MHz, CDCl3): δ=166.7 (C), 154.6 (C), 142.5 (CH), 137.5 (C), 128.0 (2CH), 126.6 (2CH), 121.1 (CH), 52.0 (CH3) ppm. 19F NMR (470 MHz, CDCl3): δ=83.7 (quint, J=150 Hz, 1 F), 62.6 (d, J=150 Hz, 4 F) ppm.
Workup
- filtrationfiltered through a pad of Celite 545 with CH2Cl2
- custompurified by SiO2 column chromatography (6:4 hexane/CH2Cl2)
Sources & evidence
- ORD record
- ord-d3db282c8dbe48f59d4e9a84046d455a
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238660B1
Reaction notes
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