Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:10](=O)[CH3:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl.[F:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[CH2:17][O:18][NH2:19]>C(OCC)(=O)C.CCCCCC>[F:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[CH2:17][O:18]/[N:19]=[C:10](/[C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([OH:1])[CH:3]=1)\[CH3:11]Participants
4
Procedure
Acetophenone 12 (50 mg, 0.301 mmol) was condensed with O-(2-fluorobenzyl)hydroxylamine hydrochloride (32) (58 mg, 0.327 mmol) according to the general procedure II-B defined above. After being heated for 36 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing residue was dissolved in CH2Cl2 (15 mL) and the resulting solution washed with H2O (2×10 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The oil thus obtained was subjected to flash chromatography (1:19 v/v ethyl acetate/hexane) to afford the title compound CP30280 (79 mg, 91%) as a pale-yellow oil, Rf 0.5 in 1:1 v/v ethyl acetate/hexane.
Workup
- temperatureAfter being heated for 36 h the reaction mixture
- temperaturewas cooled
- customthe solvent removed under reduced pressure
- dissolutionThe ensuing residue was dissolved in CH2Cl2 (15 mL)
- washthe resulting solution washed with H2O (2×10 mL)
- dry with materialthen dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe oil thus obtained
Sources & evidence
- ORD record
- ord-a1cb47cc8f73450e8f575565cb87c1e6
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536157B2
Linked notes
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