Indole-3-Acetic Acid → Methyl indole-3-acetate

HRID 652364

반응식

HRID 652364 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([OH:13])=[O:12])=[CH:2]1.S(=O)(=O)(O)O.[CH3:19]O>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([O:13][CH3:19])=[O:12])=[CH:2]1

참가 물질

4

반응물 3

HCID 802Indole-3-Acetic AcidHCID 887MethanolHCID 1118Sulfuric Acid

생성물 1

HCID 74706Methyl indole-3-acetate

실험 절차

Indole-3-acetic acid (25 g, 143 mmol) was dissolved in 500 mL of methanol and 5 mL of concentrated sulfuric acid was added. The resulting solution was heated under reflux overnight. TLC analysis indicated the absence of starting material and the reaction mixture was concentrated in vacuo. The residue was dissolved in 300 mL of ethyl ether, washed with 5% aqueous sodium bicarbonate (2×150 mL), dried over magnesium sulfate, filtered and concentrated to 24.09 g (89.1%) of the ester as a burgandy colored oil.

후처리

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux overnight
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. dissolutionThe residue was dissolved in 300 mL of ethyl ether
  5. washwashed with 5% aqueous sodium bicarbonate (2×150 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to 24.09 g (89.1%) of the ester as a burgandy colored oil

출처 및 근거

ORD 기록
ord-17223e85e3a14d79ad8fb979070471a7
출처 데이터셋
uspto-grants-1987_06
특허 번호
US04670462

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