Aluminum(III) Chloride → 2-(Hexan-2-yl)thiophene
Reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16](O)([CH2:18][CH2:19][CH2:20][CH3:21])[CH3:17]>CCOCC>[CH3:17][CH:16]([C:12]1[S:11][CH:15]=[CH:14][CH:13]=1)[CH2:18][CH2:19][CH2:20][CH3:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Under nitrogen, a suspension of LiAlH4 (4.9 g, 0.13 mol) in dry Et2O (700 mL) was cooled to 0° C. by an ice/water bath. AlCl3 (34.4 g, 0.26 mol) was then added in small portions. After addition, the mixture was stirred at 0° C. for 1 hour. A solution of 2-thiophen-2-yl-hexan-2-ol in dry Et2O (13.1 g, 70.81 mmol) was then added dropwise. The mixture was stirred at 0° C. for 2 hours, and allowed to warm to room temperature, and stirred at room temperature overnight. After cooling to 0° C., the reaction was quenched by adding water. The reaction mixture was washed with water and brine, dried over Na2SO4, and concentrated on a rotary evaporator. The residue was subjected to column chromatography on silica gel with hexane as the eluent, leading to a colorless oil as the product (6.0 g, 50.3%).
Workup
- additionAfter addition
- stirringThe mixture was stirred at 0° C. for 2 hours
- temperatureto warm to room temperature
- stirringstirred at room temperature overnight
- temperatureAfter cooling to 0° C.
- customthe reaction was quenched
- additionby adding water
- washThe reaction mixture was washed with water and brine
- dry with materialdried over Na2SO4
- concentrationconcentrated on a rotary evaporator
Sources & evidence
- ORD record
- ord-6d047036aff64ef48238a4afdff84d53
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598575B2
Reaction notes
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