Acetone → 2-(4-Aminophenyl)propan-2-ol

HRID 1924360

반응식

HRID 1924360 반응식
Br[C:2]1[CH:7]=[CH:6][C:5](/[N:8]=N/N2CCCC2)=[CH:4][CH:3]=1.[Li]C(CC)C.[CH3:20][C:21]([CH3:23])=[O:22]>CCOCC>[NH2:8][C:5]1[CH:4]=[CH:3][C:2]([C:21]([OH:22])([CH3:23])[CH3:20])=[CH:7][CH:6]=1

참가 물질

5

반응물 3

HCID 180AcetoneHCID 178418400CID 53628100HCID 178419396HCID 178419396, 화합물

생성물 1

HCID 95432612-(4-Aminophenyl)propan-2-ol수율 55.9%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
-78 °C

실험 절차

To a −78° C. solution of compound 134 (1 g, 3.95 mmol) in ether (20 mL) was added sec-BuLi (1.4 M in hexanes, 0.62 g, 9.67 mmol). The resulting solution was stirred for 30 min at −78° C., followed by addition of acetone (0.91 g, 15.81 mmol) dropwise at −78° C. The reaction mixture was warmed to room temperature overnight. The reaction mixture was partitioned between water and ether and the layers were separated. The aqueous layer was re-extracted with ether. The ether layers were the combined and concentrated in vacuo to yield crude 135 (0.33 g, 55.9%) which was used in the next step without further purification.

후처리

  1. temperatureThe reaction mixture was warmed to room temperature overnight
  2. customThe reaction mixture was partitioned between water and ether
  3. customthe layers were separated
  4. extractionThe aqueous layer was re-extracted with ether
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0059d9f2ce044afc99be9811c9af1f91
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178542B2

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