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

HRID 1034096ノート

反応式

HRID 1034096 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2f76a18addf04736869fc8be51318c07
出典データセット
uspto-grants-1994_05
特許番号
US05312829

反応ノート

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