Diisobutylaluminumhydride → 2-[2-Chloro-4-(trifluoromethoxy)phenoxy]ethan-1-ol
Reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([O:14][C:15]([F:18])([F:17])[F:16])[CH:11]=[CH:10][C:3]=1[O:4][CH2:5][C:6](OC)=[O:7].[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[Cl:1][C:2]1[CH:13]=[C:12]([O:14][C:15]([F:16])([F:18])[F:17])[CH:11]=[CH:10][C:3]=1[O:4][CH2:5][CH2:6][OH:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Methyl 2-[2-chloro-4(trifluoromethoxy)phenoxy]acetate (2.9 g, 10 mmol) was dissolved in dichloromethane (50 mL) and cooled to −78° C. A solution of diisobutylaluminum hydride in CH2Cl2 (1 M, 20 mL) was added and the reaction was warmed to 25° C. over 30 min. The reaction was quenched with methanol (2.0 mL) and poured into 0.5 N aqueous HCl. The aqueous phased was extracted with ethyl acetate and the combined organic layers were washed with brine and concetrated. The residue was chromatographed on silica gel eluting with 1:1 hexane:ethyl acetate gave 2-[2-chloro-4(trifluoromethoxy)phenoxy]ethanol.
Workup
- temperaturethe reaction was warmed to 25° C. over 30 min
- customThe reaction was quenched with methanol (2.0 mL)
- additionpoured into 0.5 N aqueous HCl
- extractionThe aqueous phased was extracted with ethyl acetate
- washthe combined organic layers were washed with brine
- customThe residue was chromatographed on silica gel eluting with 1:1 hexane
Sources & evidence
- ORD record
- ord-46e57064541c4c2f9e7cdfd6dcfc6899
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07524882B2
Reaction notes
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