Water → Methyl 3-[4-[2-(phenoxazin-10-yl)ethoxy]phenyl]-2-ethoxypropanoate

HRID 495703ノート

反応式

HRID 495703 の反応式
CS([O:5][CH2:6][CH2:7][N:8]1[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:15][C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)(=O)=O.O[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH:30]([O:35][CH2:36][CH3:37])[C:31]([O:33][CH3:34])=[O:32])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:20]1[C:21]2[N:8]([CH2:7][CH2:6][O:5][C:23]3[CH:24]=[CH:25][C:26]([CH2:29][CH:30]([O:35][CH2:36][CH3:37])[C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:28]=3)[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:15][C:16]=2[CH:17]=[CH:18][CH:19]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 112204632-(Phenoxazin-10-yl)ethyl methanesulfonateHCID 149239942-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid methyl ester

生成物 1

HCID 9824188Methyl 3-[4-[2-(phenoxazin-10-yl)ethoxy]phenyl]-2-ethoxypropanoate収率 390.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 2-(phenoxazin-10-yl)ethyl methanesulfonate (1.75 g, 5.0 mmol), methyl 3-(4-hydroxyphenyl)-2-ethoxypropanoate (1.5 g, 0.68 mmol) and potassium carbonate (3.16 g) in dry dimethylformamide (20 mL) was stirred for 12 h at 80° C. The reaction mixture was cooled to room temperature (ca. 25° C.). Water (30 mL) was added and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with water (50 mL), dried (Na2SO4) and evaporated. The residue was chromatographed using a mixture of ethyl acetate and pet. ether (1:9) to afford the title compound (1.15 g, 47%) as a white solid. mp 89-90° C. 1H NMR data matches with the desired product (see above).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature (ca. 25° C.)
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washThe combined organic extracts were washed with water (50 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was chromatographed
  7. additiona mixture of ethyl acetate and pet. ether (1:9)

出典と根拠

ORDレコード
ord-d5bfc8d7fc5b4b3383f3f72465e30523
出典データセット
uspto-grants-2005_09
特許番号
US06939988B1

反応ノート

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