1-Penten-3-one → 5-Amino-4-bromo-2-ethyl-2-(3-oxopentyl)-1-indanone
Reaction equation
C([NH:4][C:5]1[C:6]([Br:17])=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[CH:9]([CH2:15][CH3:16])[CH2:8]2)(=O)C.C[O-].[Na+].[CH:21]([C:23]([CH2:25][CH3:26])=[O:24])=[CH2:22]>CO>[NH2:4][C:5]1[C:6]([Br:17])=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[C:9]([CH2:15][CH3:16])([CH2:22][CH2:21][C:23](=[O:24])[CH2:25][CH3:26])[CH2:8]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A solution of 5-(acetylamino)-4-bromo-2-ethyl-1-indanone (1.0 g, 3.39 mmol) in MeOH (5.1 mL) was treated with 0.5M NaOMe in MeOH (3.4 mL, 1.7 mmol) and ethyl vinyl ketone (0.506 mL, 5.08 mmol). The mixture was stirred and heated at 60° C. for 4.5 hours, then evaporated under vacuum. The residue was partitioned between EtOAc (75 mL), brine (50 mL), and water (10 mL). The organic portion was dried over MgSO4, filtered, and evaporated under vacuum. The residue was added to a short column of silica gel (30 mL) which was washed with CH2Cl2 (150 mL) and eluted with EtOAc (150 mL). The EtOAc eluant was evaporated under vacuum to provide crude 5-amino-4-bromo-2-ethyl-2-(3-oxopentyl)-1-indanone (1.17 g) as an oil.
Workup
- customevaporated under vacuum
- customThe residue was partitioned between EtOAc (75 mL), brine (50 mL), and water (10 mL)
- dry with materialThe organic portion was dried over MgSO4
- filtrationfiltered
- customevaporated under vacuum
- additionThe residue was added to a short column of silica gel (30 mL) which
- washwas washed with CH2Cl2 (150 mL)
- washeluted with EtOAc (150 mL)
- customThe EtOAc eluant was evaporated under vacuum
Sources & evidence
- ORD record
- ord-f306aa7ddea34de68a7af81adb81b4f8
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07157604B2
Reaction notes
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