Water → 2-Ethoxy-3-{4-[2-(4-phenylmethanesulfonyloxyphenyl)ethoxy]phenyl}propanoic acid ethyl ester

HRID 987255ノート

反応式

HRID 987255 の反応式
[CH2:1]([O:3][C:4](=[O:26])[CH:5]([O:23][CH2:24][CH3:25])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)[CH3:2].C(N(CC)CC)C.[CH2:34]([S:41](Cl)(=[O:43])=[O:42])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.O>ClCCl>[CH2:1]([O:3][C:4](=[O:26])[CH:5]([O:23][CH2:24][CH3:25])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][S:41]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)(=[O:43])=[O:42])=[CH:20][CH:21]=2)=[CH:9][CH:8]=1)[CH3:2]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 74740Phenylmethanesulfonyl chlorideHCID 54239207HCID 54239207、化合物

生成物 1

HCID 865950622-Ethoxy-3-{4-[2-(4-phenylmethanesulfonyloxyphenyl)ethoxy]phenyl}propanoic acid ethyl ester収率 71.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

2-Ethoxy-3-{4-[2-(4-hydroxyphenyl)ethoxy]phenyl}propanoic acid ethyl ester (described in Example 26b) (0.54 g; 1.5 mmole) was dissolved in dichloromethane (15 ml), triethylamine (0.23 g; 0.31 ml; 2.25 mmole) was added. The solution was cooled to 0° C. and benzylsulfonyl chloride (0.43 g; 2.25 mmole) dissolved in dichloromethane (5 ml) was added. The resulting mixture was allowed to reach room temperature and was stirred over night. Water was added, the organic layer separated and the water phase extracted with dichloromethane. The organic phase was washed with hydrochloric acid (1 M), sodium hydrogen carbonate and brine. After drying with sodium sulfate and evaporation a light yellow oil was obtained. The crude product was purified with flash chromatography on silica. The compound was eluated with heptane:ethyl acetate (9:1 followed by 1:1). Pure fractions were pooled and evaporated yielding 0.55 g (71%) of 2-ethoxy-3-{4-[2-(4-phenylmethanesulfonyloxyphenyl)ethoxy]phenyl}propanoic acid ethyl ester.

後処理

  1. additionwas added
  2. customto reach room temperature
  3. customthe organic layer separated
  4. extractionthe water phase extracted with dichloromethane
  5. washThe organic phase was washed with hydrochloric acid (1 M), sodium hydrogen carbonate and brine
  6. dry with materialAfter drying with sodium sulfate and evaporation a light yellow oil
  7. customwas obtained
  8. customThe crude product was purified with flash chromatography on silica
  9. customevaporated

出典と根拠

ORDレコード
ord-e55dcf706bb4411886dfaf03683a9af6
出典データセット
uspto-grants-2003_10
特許番号
US06630600B1

反応ノート

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