Dimethylformamide → 2-Acetoxy-1-(naphth-1-yl)-1-propanone

HRID 33572노트

반응식

HRID 33572 반응식
Br[CH:2]([CH3:15])[C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4].[C:16]([O-:19])(=[O:18])[CH3:17].[Na+].CN(C)C=[O:24]>>[C:5]1([CH:3]([O:4][C:16](=[O:18])[CH3:17])[C:2](=[O:24])[CH3:15])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.[CH3:15][CH:2]([O:19][C:16](=[O:18])[CH3:17])[C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4]

참가 물질

5

반응물 3

HCID 6228Dimethylformamide2회HCID 2311612-Bromo-1'-propionaphthoneHCID 517045Sodium Acetate

생성물 2

HCID 51033133Acetic acid 1-naphthalen-1-yl-2-oxo-propyl esterHCID 597968292-Acetoxy-1-(naphth-1-yl)-1-propanone수율 49%

반응 조건

온도
80 °C

실험 절차

A mixture of 2-bromo-1-naphthalen-1-yl-propan-1-one (20 g), sodium acetate (7.8 g) and N,N-dimethylformamide (300 mL) was heated at 80° C. for 18 hours. After cooling to room temperature the N,N-dimethylformamide was removed under reduced pressure and the resulting residue was partitioned between dichloromethane (300 mL) and water (300 mL). The organic phase was washed with water (300 mL), brine (300 mL), dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to afford acetic acid 1-naphthalen-1-yl-2-oxo-propyl ester and acetic acid 1-methyl-2-naphthalen-1-yl-2-oxo-ethyl ester (2:1 mixture) (9.0 g, 49%) as a brown oil, 1H NMR (CDCl3): 1.45 (3H, d, J=7.0 Hz), 2.05 (3H, s), 2.15 (3H, s), 2.2 (3H, s), 5.95 (1H, q, J=7.0 Hz), 6.65 (1H, s), 7.45-7.60 (7H, m), 7.85-7.90 (4H, m), 8.0 (1H, d, J=8.1 Hz), 8.1 (1H, d, J=8.3 Hz), 8.35 (1H, d, J=8.6 Hz).

후처리

  1. customwas removed under reduced pressure
  2. customthe resulting residue was partitioned between dichloromethane (300 mL) and water (300 mL)
  3. washThe organic phase was washed with water (300 mL), brine (300 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

출처 및 근거

ORD 기록
ord-00208282f9144c10a73a4b4b26773f68
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429607B2

반응 노트

불러오는 중…