Water → 1-[3-(Dimethylamino)phenyl]-1-butanone

HRID 573554

반응식

HRID 573554 반응식
Br[C:2]1[CH:3]=[C:4]([N:8]([CH3:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.CN(OC)[C:18](=[O:22])[CH2:19][CH2:20][CH3:21].O>C1COCC1.C(OCC)(=O)C>[CH3:9][N:8]([CH3:10])[C:4]1[CH:3]=[C:2]([C:18](=[O:22])[CH2:19][CH2:20][CH3:21])[CH:7]=[CH:6][CH:5]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 1401023-Bromo-N,N-dimethylanilineHCID 13704543N-Methoxy-N-methylbutyramideHCID 178418339Butyllithium

생성물 1

HCID 672368851-[3-(Dimethylamino)phenyl]-1-butanone수율 48.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
-35 °C

실험 절차

To a stirred solution of (3-bromophenyl)dimethylamine (7.5 g, 37.5 mmol) in THF (50 mL) at −78° C., was added n-butyllithium (2.88 g, 45.0 mmol). The resulting solution was stirred at −35° C. for 1 h and was then cooled to −78° C. and treated dropwise with a solution of N-methyl-N-(methyloxy)butanamide (4.92 g, 37.5 mmol) (Description 25) in dry THF (15 mL). The resulting mixture was stirred for 45 min at −78° C. and then worked up using water (100 mL) and ethyl acetate (200 mL). The crude material was purified by chromatography on silica gel, eluting with a gradient of 0-20% ethyl acetate in hexane, to afford the title compound (3.48 g). LCMS (B) m/z: 192 [M+1]+, Rt 2.29 min.

후처리

  1. temperaturewas then cooled to −78° C.
  2. stirringThe resulting mixture was stirred for 45 min at −78° C.
  3. customThe crude material was purified by chromatography on silica gel
  4. washeluting with a gradient of 0-20% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-50373b997a7d4bc2b122044b8e214d1d
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029545B2

연결된 노트

불러오는 중…