Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([C:15]2[O:19][C:18](/[CH:20]=[CH:21]/[NH2:22])=[CH:17][CH:16]=2)[CH:11]=[CH:12][C:13]=1[Cl:14].CO.O>C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10]([C:15]2[O:19][C:18]([CH2:20][CH2:21][NH2:22])=[CH:17][CH:16]=2)[CH:11]=[CH:12][C:13]=1[Cl:14]Participants
Procedure
To a suspension of lithium aluminium hydride (0.939 g, 24.8 mmol) in THF (20 ml) under nitrogen atmosphere at 0° C. was added slowly a solution of (E)-2-(5-(3,4-dichlorophenyl)furan-2-yl)ethenamine in THF (20 ml). Reaction mixture was stirred at RT for 1 h. Some methanol was added slowly to the mixture followed by addition of water. The mixture was evaporated, and the solid residue was extracted with EtOAc (3×). Combined EtOAc fractions were washed with 2M NaOH and brine. Organic phase was dried over Na2SO4, evaporated and purified by chromatography (CombiFlash, silica column, eluent: 10-20% MeOH/DCM) to give 227 mg (11%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 2.74 (t, 2H), 2.85 (t, 2H), 6.29 (d, 1H), 7.03 (d, 1H), 7.62 (dd, 1H), 7.63 (d, 1H), 7.88 (d, 1H).
Workup
- customReaction mixture
- customThe mixture was evaporated
- extractionthe solid residue was extracted with EtOAc (3×)
- washCombined EtOAc fractions were washed with 2M NaOH and brine
- dry with materialOrganic phase was dried over Na2SO4
- customevaporated
- custompurified by chromatography (CombiFlash, silica column, eluent: 10-20% MeOH/DCM)
Sources & evidence
- ORD record
- ord-2f018cd5f6d549a9bd89f8d2f2e52d79
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975254B2
Linked notes
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