Lithium diisopropylamide → (5-Chlorobenzofuran-3-yl)methanol
Reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH2:7]N2C3C=CC=CC=3N=N2)=[C:4]([CH:19]2[CH2:21][O:20]2)[CH:3]=1.[Li+].CC([N-]C(C)C)C>O1CCCC1>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[O:6][CH:7]=[C:19]([CH2:21][OH:20])[C:4]=2[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
99 (25.7 g, 85.1 mmol) is dissolved in 300 ml of tetrahydrofurane and cooled to −78° C. A 2M solution of LDA in THF (93.7 ml, 187.4 mmol) is added dropwise within 45 min. The reaction mixture is allow to warmup to room temperature within 17 h. Then the reaction mixture is quenched with saturated aqueous ammonium chloride solution and evaporated under reduced pressure. The residue is diluted with ethyl acetate, washed with water and brine and dried over sodium sulfate. Evaporation gave 17.2 g of an brown resin which is further purified by flash-chromatography (silicagel, ethyl acetate/hexanes 2:8).
Workup
- customThen the reaction mixture is quenched with saturated aqueous ammonium chloride solution
- customevaporated under reduced pressure
- additionThe residue is diluted with ethyl acetate
- washwashed with water and brine
- dry with materialdried over sodium sulfate
- customEvaporation
Sources & evidence
- ORD record
- ord-36feea2beae1476e8792fb93dca4fe94
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08183366B2
Reaction notes
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