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

HRID 33572ノート

反応式

HRID 33572 の反応式
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]

参加物

5

反応物 3

HCID 6228Dimethylformamide2 回HCID 2311612-Bromo-1'-propionaphthoneHCID 517045Sodium Acetate

生成物 2

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

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-00208282f9144c10a73a4b4b26773f68
出典データセット
uspto-grants-2008_09
特許番号
US07429607B2

反応ノート

読み込み中…