2'-Methoxyacetophenone → (1R)-1-(2-methoxyphenyl)ethan-1-ol

HRID 1349447ノート

反応式

HRID 1349447 の反応式
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.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31](=[O:33])[CH3:32]>O1CCCC1>[CH3:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C@H:31]([OH:33])[CH3:32]

参加物

4

反応物 2

HCID 684812'-MethoxyacetophenoneHCID 9923113Chlorobis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo(3.1.1)hept-3-yl)borane

生成物 1

HCID 643317(1R)-1-(2-methoxyphenyl)ethan-1-ol収率 75.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-25 °C

実験手順

To a solution of (+)-B-chlorodiisopinocampheylborane (10.5 g) in tetrahydrofuran (50 ml) was added dropwise 2′methoxyacetophenone (10.5 g) at −25° C. The mixture was stirred at −25° C. for 1 hr and concentrated under reduced pressure. To the residue were added diethyl ether (100 ml) and diethanolamine (18.1 g) and the reaction mixture was stirred at room temperature for 2 hr. The precipitated solid was filtered off. The filtrate was concentrated under reduced pressure and purified by distillation under reduced pressure (bp 74–77° C./1 mmHg) to give the title compound (8.00 g).

後処理

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue were added diethyl ether (100 ml) and diethanolamine (18.1 g)
  3. stirringthe reaction mixture was stirred at room temperature for 2 hr
  4. filtrationThe precipitated solid was filtered off
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. distillationpurified by distillation under reduced pressure (bp 74–77° C./1 mmHg)

出典と根拠

ORDレコード
ord-dd27a7b685d449708c8f368841ab3425
出典データセット
uspto-grants-2007_05
特許番号
US07211685B2

反応ノート

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