Hydrochloric Acid → HCID 19045524, compound
Reaction equation
B.[O:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[C:7]([N:10]1[C:18]2[C:13](=CC(C=C)=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)(=[O:9])[CH3:8].O.O.C[N+]([O-])(C)C.Cl>O>[C:7]([N:10]1[C:18]2[C:13](=[CH:3][C:4]([CH2:5][CH2:6][OH:2])=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)(=[O:9])[CH3:8]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Borane-tetrahydrofuran complex (1.0M in THF, 20 ml, 20 mmol) was added dropwise to an ice cooled solution of 1-acetyl-2,3-dihydro-5-ethenyl-1H-indole (5.61 g, 30 mmol) in TEF (150 ml). The mixture was stirred at 0° C. for 30 minute then at room temperature for 1 hr. Trimethylamine N-oxide dihydrate (8.88 g, 80 mmol) was added and the mixture was heated under reflux for 3 hr, cooled and poured into water (400 ml) and aqueous HCl (6N, 10 ml). The mixture was extracted with dichloromethane (3×400 ml) and the combined organic fractions were dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate, to give the alcohol as a white solid (3.41 g, 55%).
Workup
- waitat room temperature for 1 hr
- temperaturethe mixture was heated
- temperatureunder reflux for 3 hr
- temperaturecooled
- extractionThe mixture was extracted with dichloromethane (3×400 ml)
- dry with materialthe combined organic fractions were dried (Na2SO4)
- customevaporated under reduced pressure
- customThe residue was purified by flash column chromatography on silica gel
- washeluting with ethyl acetate
Sources & evidence
- ORD record
- ord-b220a1fa1ec249d1b183fede606be887
- Source dataset
- uspto-grants-1997_05
- Patent number
- US05633247
Reaction notes
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