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

HRID 1034096노트

반응식

HRID 1034096 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2f76a18addf04736869fc8be51318c07
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05312829

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