Methanol → methyl 1H-indole-5-carboxylate

HRID 14156

반응식

HRID 14156 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH2:13](N(CC)CC)C.CO>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

참가 물질

5

반응물 3

HCID 887MethanolHCID 8471TriethylamineHCID 742801H-Indole-5-Carboxylic Acid

생성물 1

HCID 2737635methyl 1H-indole-5-carboxylate수율 24.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of indole-5-carboxylic acid (3.0 g) and triethylamine (1.9 g) in dry THF (100 mL) was added 1,1-carbonyldiimidazole (3.08 g). The mixture was stirred for 30 minutes at room temperature, at which time methanol (25 mL) was added. The mixture was stirred at room temperature for 1 h, partitioned between water and ethyl acetate. The layers were separated and the organic layer washed twice with water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Column chromatography on silica gel (200 mL) using CH2Cl2 as eluent to give 0.794 g of the title compound: 1H NMR (CDCl3) δ 3.93, 6.66, 7.28, 7.41, 7.91, 8.34, 8.42.

후처리

  1. additionwas added
  2. custompartitioned between water and ethyl acetate
  3. customThe layers were separated
  4. washthe organic layer washed twice with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-f2cb02f730614ea9bba022c7429056cc
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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