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Citric Acid → tert-Butyl 3-(hydroxymethyl)-1H-indole-1-carboxylate

HRID 2422242
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HRID 2422242 반응식
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17](OC)=[O:18])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][OH:18])=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

반응물 3

HCID 311Citric AcidHCID 299461281-tert-Butyl 3-methyl 1H-indole-1,3-dicarboxylateHCID 86583787Diisobutylaluminumhydride toluene

생성물 1

HCID 11075767tert-Butyl 3-(hydroxymethyl)-1H-indole-1-carboxylate수율 102.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 1-(tert-butoxycarbonyl)-1H-indole-3-carboxylate (2.5 g, 9.08 mmol) in anhydrous tetrahydrofuran (40 ml) was added 1.5 M diisobutylaluminum hydride-toluene solution (14 ml, 21 mmol) under ice-cooling, and the mixture was stirred for 2 hrs. An aqueous citric acid solution was added, and the mixture was extracted with ethyl acetate. The extract was washed successively with aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (2.3 g, 100%) as a pale-yellow oil.

후처리

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed successively with aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-fbaecb139f954bea84ac99428f5debb2
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07960369B2

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