Water → Tert-butyl 4-(2-(dimethylamino)ethoxy)-2-nitrobenzoate

HRID 1921088ノート

反応式

HRID 1921088 の反応式
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].CC(C)([O-])C.[K+].[C:13]([O:17][C:18](=[O:29])[C:19]1[CH:24]=[CH:23][C:22](F)=[CH:21][C:20]=1[N+:26]([O-:28])=[O:27])([CH3:16])([CH3:15])[CH3:14].O>C1COCC1>[C:13]([O:17][C:18](=[O:29])[C:19]1[CH:24]=[CH:23][C:22]([O:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[CH:21][C:20]=1[N+:26]([O-:28])=[O:27])([CH3:16])([CH3:14])[CH3:15]

参加物

6

反応物 4

HCID 962WaterHCID 79022-(Dimethylamino)ethanolHCID 23665647Potassium tert-butoxideHCID 57447321Tert-butyl 4-fluoro-2-nitrobenzoate

生成物 1

HCID 57447330Tert-butyl 4-(2-(dimethylamino)ethoxy)-2-nitrobenzoate収率 35.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of 2-dimethylaminoethanol (6.67 mL, 64.8 mmol) in anhydrous THF (100 mL), at 0° C., potassium tert-butoxide (6.66 g, 59.4 mmol) was added. The mixture was stirred at 0° C. for 1 h, then 4-fluoro-2-nitro-benzoic acid tert-butyl ester (10 g, 41.5 mmol) in anhydrous THF (50 mL) was added dropwise. After 2 hours at 0° C., the mixture was poured into water (1 L) and extracted with ethyl acetate (4×200 mL). The organic phase was washed with water, brine, dried with anhydrous sodium sulfate, filtered and evaporated to dryness. The crude was purified by flash chromatography, using dichloromethane-EtOH-33% NH4OH 9:1:0.01 as eluant, to give the title compound (4.53 g) as yellow oil.

後処理

  1. waitAfter 2 hours at 0° C.
  2. extractionextracted with ethyl acetate (4×200 mL)
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude was purified by flash chromatography

出典と根拠

ORDレコード
ord-71ba93b5f4e84e28b8876bd92a72f118
出典データセット
uspto-grants-2012_05
特許番号
US08173659B2

反応ノート

読み込み中…