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

HRID 1349447노트

반응식

HRID 1349447 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-25 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-dd27a7b685d449708c8f368841ab3425
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07211685B2

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