Chlorobis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo(3.1.1)hept-3-yl)borane → (R)-1-(4-isobutylphenyl)pentan-1-ol

HRID 1034096Notes

Reaction equation

HRID 1034096 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:16])[CH2:12][CH2:13][CH2:14][CH3:15])=[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:16])[CH2:12][CH2:13][CH2:14][CH3:15])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 9923113Chlorobis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo(3.1.1)hept-3-yl)boraneHCID 109984904'-Isobutylpentanophenone

Product 1

HCID 11074925(R)-1-(4-isobutylphenyl)pentan-1-olYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4'-Isobutylpentanophenone (2.1 g) was added to a solution of (+)-B-chlorodiisopinocampheylborane (3.57 g) in tetrahydrofuran (7 ml) at -25° C. After stirring for 5 hours, the solvent was removed and the residue was dissolved in ethyl ether (30 ml). To this solution was added diethanolamine (2 ml), 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 (hexane:dichloromethane =1:2) to give (R)-1-(4-isobutylphenyl)pentan-1-ol (635 mg).

Workup

  1. customthe solvent was removed
  2. dissolutionthe residue was dissolved in ethyl ether (30 ml)
  3. additionTo this solution was added diethanolamine (2 ml)
  4. stirringthe mixture was stirred for 2 hours
  5. filtrationThe solid was filtered off
  6. washwashed with ethyl ether
  7. concentrationThe combined filtrates were concentrated
  8. customthe residue was chromatographed on silica gel (hexane:dichloromethane =1:2)

Sources & evidence

ORD record
ord-2f76a18addf04736869fc8be51318c07
Source dataset
uspto-grants-1994_05
Patent number
US05312829

Reaction notes

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