Dimethyl Sulfoxide → 2-[1-(3-chloropropyl)-1H-indol-4-yloxy]-2-methylpropionic acid ethyl ester

HRID 269953

反応式

HRID 269953 の反応式
[CH2:1]([O:3][C:4](=[O:18])[C:5]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2)([CH3:7])[CH3:6])[CH3:2].[OH-].[K+].CS(C)=O.Br[CH2:26][CH2:27][CH2:28][Cl:29]>O>[CH2:1]([O:3][C:4](=[O:18])[C:5]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH2:26][CH2:27][CH2:28][Cl:29])([CH3:7])[CH3:6])[CH3:2]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 80061-Bromo-3-chloropropaneHCID 14797Potassium HydroxideHCID 160908702-(1H-indol-4-yloxy)-2-methylpropionic acid ethyl ester

生成物 1

HCID 160908732-[1-(3-chloropropyl)-1H-indol-4-yloxy]-2-methylpropionic acid ethyl ester収率 98%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

2-(1H-Indol-4-yloxy)-2-methylpropionic acid ethyl ester (0.100 g, 0.40 mmol, 1.0 eq), powdered potassium hydroxide (0.034 g, 0.61 mmol, 1.5 eq), and DMSO (3 mL) were mixed and stirred at room temperature for 10 minutes. 1-Bromo-3-chloropropane (0.12 mL, 0.191 g, 1.21 mmol, 3.0 eq) was then added to the above mixture. The reaction mixture was stirred at room temperature for another 1.5 hours before 15 mL of water was added. The mixture was extracted with ethyl acetate (2×30 mL). The organic layer was collected, combined, washed with water (6×25 mL) and brine (2×20 mL), and dried over anhydrous Na2SO4. The solvent was removed in vacuo to afford 2-[1-(3-chloropropyl)-1H-indol-4-yloxy]-2-methylpropionic acid ethyl ester (0.127 g, yield: 97%) as a dense oily liquid, which was used for the next step without further purification.

後処理

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate (2×30 mL)
  3. customThe organic layer was collected
  4. washwashed with water (6×25 mL) and brine (2×20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-ac71b308e6764506acda086ceb619d3e
出典データセット
uspto-grants-2008_11
特許番号
US07449478B2

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