Aluminium lithium hydride → HCID 22504181, compound
Reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH2:12][C:13](=[O:15])[CH3:14].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH2:12][CH:13]([OH:15])[CH3:14]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
1-(2-Methyl-naphthalen-1-yl)-propan-2-one (1.14 g, 5.76 mmol) was dissolved in Et2O (30 mL) in an argon-purged, round-bottom flask. The mixture was chilled to −78° C. and LiAlH4 (438 mg, 11.52 mmol) was added. The reaction was stirred at −78° C. for five minutes and then at room temperature for twenty minutes. TLC analysis (silica, 20% EtOAc-hexanes) indicated the reaction was complete. The reaction was chilled again to −78° C. and was carefully quenched with saturated aqueous KHSO4 (˜2 mL). The mixture was warmed to room temperature, diluted with H2O, and extracted three times with EtOAc. The organic extracts were combined, washed with brine solution, dried over Na2SO4, filtered through celite, and concentrated to give 1-(2-methyl-naphthalen-1-yl)-propan-2-ol in quantitative yield. MS (APCI) m/z 200.2 (M−H).
Workup
- custompurged
- waitat room temperature for twenty minutes
- temperatureThe reaction was chilled again to −78° C.
- customwas carefully quenched with saturated aqueous KHSO4 (˜2 mL)
- temperatureThe mixture was warmed to room temperature
- additiondiluted with H2O
- extractionextracted three times with EtOAc
- washwashed with brine solution
- dry with materialdried over Na2SO4
- filtrationfiltered through celite
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b066ec970db140c69c3a37b0f58bbb1f
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06875765B2
Reaction notes
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