Diethanolamine → Benzenemethanol, 2,4-dichloro-α-methyl-, (αR)-
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].B(Cl)([C@@H]1[C@@H](C)[C@H]2C(C)(C)[C@H](C2)C1)[C@@H]1[C@@H](C)[C@H]2C(C)(C)[C@H](C2)C1.N(CCO)CCO>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C@H:9]([OH:11])[CH3:10]Participants
5
Conditions
- Temperature
- -25 °C
Procedure
To a solution of 2′,4′-dichloroacetophenone (10.9 g, 77.0 mmol) in anhydrous THF (80 mL) at −78° C. under nitrogen was slowly added a solution of (+)-B-chlorodiisopinocampheylborane ((+)-Ipc2BCl, 27.2, 85.0 mmol) in THF (15 mL). After the addition is complete, the reaction mixture was slowly warmed to −25° C. and stirred at this temperature for 2 h. The reaction mixture was then quenched with diethanolamine (17.9 g, 170 mmol), and stirred for 10 min. During this time, a solid formed and it was filtered off. The filtrate was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified flash chromatography (SiO2, 0-20% ethyl acetate in hexanes) to give (R)-1-(2,4-dichlorophenyl)ethanol (12.0 g, 63.3 mmol, 82%).
Workup
- additionAfter the addition
- stirringstirred for 10 min
- customDuring this time, a solid formed
- filtrationit was filtered off
- dry with materialThe filtrate was dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified flash chromatography (SiO2, 0-20% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-61a611dd92cd48f8b911ab1b1fe69787
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08685959B2
Reaction notes
Loading…