Magnesium perchlorate → Methyl 3-(5-methoxy-1H-indol-3-yl)propanoate

HRID 384869

반응식

HRID 384869 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12]O.[CH3:14][O:15][C:16]([O:20][Si](C)(C)C)=[C:17](C)C.Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O>ClCCl.O>[CH3:14][O:15][C:16](=[O:20])[CH2:17][CH2:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:8][CH:7]=1

참가 물질

6

반응물 3

HCID 24840Magnesium perchlorateHCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 4255293(5-methoxy-1H-indol-3-yl)methanol

생성물 1

HCID 54357260Methyl 3-(5-methoxy-1H-indol-3-yl)propanoate수율 100%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 5-methoxy-1H-indol-3-yl-methanol 141 (115 mg, 0.643 mmol) dissolved in dichloromethane (3 ml), (1-methoxy-2-methyl-propenyloxy)-trimethylsilane (200 mg, 1 mmol) and magnesium perchlorate (164 mg, 0.74 mmol) were added. The reaction was allowed to stir at ambient temperature for 3-4 hours after which the mixture was diluted with water (50 ml) and dichloromethane (DCM, 100 mL). The organic layer was separated and washed with water (50 mL; 3×). The organic layer was washed once with brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to give an oil and purified with flash chromatography (silica with 80% hexane, 20% ethyl acetate to afford 142 as a light colored oil (150 mg; 88% yield; M+1=262.3).

후처리

  1. customThe organic layer was separated
  2. washwashed with water (50 mL; 3×)
  3. washThe organic layer was washed once with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customto give an oil
  7. custompurified with flash chromatography (silica with 80% hexane, 20% ethyl acetate

출처 및 근거

ORD 기록
ord-28ec998738a3433390f28c728015bb0c
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367828B2

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