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

HRID 269953

반응식

HRID 269953 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ac71b308e6764506acda086ceb619d3e
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449478B2

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