Propargyl alcohol → HCID 58822792, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C@@H:5]([O:21][CH3:22])[CH2:6][C:7]1[CH:12]=[CH:11][C:10](OS(C(F)(F)F)(=O)=O)=[CH:9][CH:8]=1)[CH3:2].[CH2:24]([OH:27])[C:25]#[CH:26].C(N(CC)CC)C>CN(C=O)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:23])[C@@H:5]([O:21][CH3:22])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:26]#[C:25][CH2:24][OH:27])=[CH:9][CH:8]=1)[CH3:2]Participants
Procedure
A solution of (2S)-2-methoxy-3-(4-trifluoromethane-sulfonyloxy-phenyl)-propionic acid ethyl ester (0.861 g, 2.53 mmol), propargyl alcohol (0.88 mL, 15.18 mmol), triethylamine (1.41 mL, 10.12 mmol) and dichlorobis(triphenylphosphine)palladium (II) in 10 mL of dry DMF was heated to 90° C. for 2 hours. The reaction mixture was cooled to room temperature, diluted with 50 mL of water, and extracted with diethyl ether (3×30 mL). The combined organic layers were washed with 0.5 N HCl (2×20 mL) and brine (20 mL), dried (MgSO4), and concentrated. The residue purified by column chromatography (silica gel, hexanes/ethyl acetate 2:1, Rf0.17) to give a yellow-brown oil (0.211 g, 32%). 1H-NMR (200.15 MHz, CDCl3): δ 7.35 (d, 2H, J=8.1), 7.18 (d, 2H, J=8.1), 4.48 (s, 2H), 4.17 (q, 2H, J=7.3), 3.93 (dd, 1H, J=7.3, 5.7), 3.34 (s, 3H), 3.02 (s, 1H), 2.99 (d, 1H, J=2.2), 1.8 (s, 1H), 1.22 (t, 3H, J=7.3).
Workup
- extractionextracted with diethyl ether (3×30 mL)
- washThe combined organic layers were washed with 0.5 N HCl (2×20 mL) and brine (20 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe residue purified by column chromatography (silica gel, hexanes/ethyl acetate 2:1, Rf0.17)
Sources & evidence
- ORD record
- ord-918ff3500f974fa3b6b0bcf686fd3edc
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07192982B2
Reaction notes
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