Chlorobis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo(3.1.1)hept-3-yl)borane → HCID 11063606, compound
Reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:15])[CH2:12][CH2:13][CH3:14])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].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>O1CCCC1>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C@H:11]([OH:15])[CH2:12][CH2:13][CH3:14])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4'-Isobutylbutanophenone (1.2 g) was added to a solution of (+)-B-chlorodiisopinocampheylborane (2.10 g) in tetrahydrofuran (4 ml) at 25° C. After 5 hours, the solvent was removed and the residue was dissolved in ethyl ether (20 ml). Diethanolamine (1.4 ml) was added to the mixture and the mixture was stirred for 2 hours. The solid was filtered off and washed with ethyl ether. The combined filtrates were concentrated and the residue was chromatographed on silica gel (eluent:hexane:CH2Cl2 =1:2) to give (R)-1-(4-isobutylphenyl)butan-1-ol (937 mg).