1-Bromopentane → Pentyl 4-methoxy-3-pentyloxycinnamate

HRID 850446

反応式

HRID 850446 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH:5]=[CH:6][C:7]([OH:9])=[O:8].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:14][O:13][C:12]1[CH:11]=[CH:10][C:4]([CH:5]=[CH:6][C:7]([O:9][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:8])=[CH:3][C:2]=1[O:1][CH2:11][CH2:12][CH2:2][CH2:3][CH3:4]

参加物

5

反応物 3

HCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 921263-(3-Hydroxy-4-methoxyphenyl)prop-2-enoic acid

生成物 1

HCID 54536911Pentyl 4-methoxy-3-pentyloxycinnamate収率 217.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

3-Hydroxy-4-methoxycinnamic acid (9.7 g, 0.050 mol, 1.0 eq) was dissolved in DMF (90 ml). 1-Bromopentane (22.7 g, 0.150 mol, 3.0 eq) and anhydrous potassium carbonate (41.5 g, 0.30 mol, 6.0 eq) were successively added to this solution, and the mixture was stirred under heating at 90° C. for 3 hours. This reaction mixture was cooled to room temperature, and anhydrous potassium carbonate was filtered off. Water (200 ml) was added to the filtrate, and the mixture was exracted twice with ethyl acetate (200 ml). The organic layers were combined, washed with saturated brine (300 ml) and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (n-hexane/ethyl acetate=15/1-10/1) to give pentyl 4-methoxy-3-pentyloxycinnamate (18.2 g, 100%) as a colorless oil.

後処理

  1. temperatureThis reaction mixture was cooled to room temperature
  2. filtrationanhydrous potassium carbonate was filtered off
  3. additionWater (200 ml) was added to the filtrate
  4. washwashed with saturated brine (300 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe drying agent was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by column chromatography (n-hexane/ethyl acetate=15/1-10/1)

出典と根拠

ORDレコード
ord-d0b1d754534f478bbff696545eb58029
出典データセット
uspto-grants-2000_01
特許番号
US06017919

関連ノート

読み込み中…