Hydrochloric Acid → methyl 3-cyclohexyl-2-(2,4-dihydroxyphenyl)-1-(2-hydroxyethyl)-1H-indole-6-carboxylate

HRID 1012248노트

반응식

HRID 1012248 반응식
COC[O:4][C:5]1[CH:10]=[C:9]([O:11]COC)[CH:8]=[CH:7][C:6]=1[C:15]1[N:16]([CH2:34][CH2:35][O:36]C2CCCCO2)[C:17]2[C:22]([C:23]=1[CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[CH:21][CH:20]=[C:19]([C:30]([O:32][CH3:33])=[O:31])[CH:18]=2.Cl>CO.O1CCCC1>[CH:24]1([C:23]2[C:22]3[C:17](=[CH:18][C:19]([C:30]([O:32][CH3:33])=[O:31])=[CH:20][CH:21]=3)[N:16]([CH2:34][CH2:35][OH:36])[C:15]=2[C:6]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:5]=2[OH:4])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 58826635methyl 2-(2,4-bismethoxymethoxyphenyl)-3-cyclohexyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1H-indole-6-carboxylate

생성물 1

HCID 23152674methyl 3-cyclohexyl-2-(2,4-dihydroxyphenyl)-1-(2-hydroxyethyl)-1H-indole-6-carboxylate수율 68%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 2-(2,4-bismethoxymethoxyphenyl)-3-cyclohexyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1H-indole-6-carboxylate in methanol (525 ml) and tetrahydrofuran (30 ml) was added 6N hydrochloric acid (105 ml) and the mixture was stirred for 10 hr. The reaction mixture was concentrated and water was added. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=1:1) to give methyl 3-cyclohexyl-2-(2,4-dihydroxyphenyl)-1-(2-hydroxyethyl)-1H-indole-6-carboxylate (10.3 g, yield 68%).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customthe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-08009d51d67442ec9942ced5ead8ed52
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977331B1

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