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Aluminium lithium hydride → HCID 59814778, 화합물

HRID 2116726
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HRID 2116726 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([Si:11]([CH3:26])([CH3:25])[O:12][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[C:18]([C:22](O)=[O:23])[NH:19]2)=[CH:15][CH:14]=1)([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[C:7]([Si:11]([CH3:26])([CH3:25])[O:12][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[C:18]([CH2:22][OH:23])[NH:19]2)=[CH:15][CH:14]=1)([CH3:10])([CH3:9])[CH3:8]
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참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 68949735HCID 68949735, 화합물

생성물 1

HCID 59814778HCID 59814778, 화합물수율 40.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

1M LAH in THF (103 ml) is cooled to 0° C. A solution of 6-(tert-Butyl-dimethyl-silanyloxy)-1H-indole-2-carboxylic acid (6.0 g, 20.60 mmol) in THF (30 ml) is added slowly. The reaction is stirred at room temperature for two days, quenched with water (10 ml), 1N NaOH (10 ml) and water (20 ml). To the mixture MgSO4 is added. The mixture is filtered, washed with 10% methanol in ethyl acetate (200 ml). The filtrate is concentrated to oil. The crude is purified by column chromatography (20% ethyl acetate in hexanes) to provide [6-(tert-Butyl-dimethyl-silanyloxy)-1H-indol-2-yl]-methanol (2.30 g, 40% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.72 (s,1H) , 7.28 (d, 1H), 6.76 (s,1H), 6.50 (m,1H), 6.16 (s,1H), 5.13 (t, 1H), 4.52 (d, 2H), 0.96 (s, 9H), 0.17 (s, 6H).

후처리

  1. customquenched with water (10 ml), 1N NaOH (10 ml) and water (20 ml)
  2. additionTo the mixture MgSO4 is added
  3. filtrationThe mixture is filtered
  4. washwashed with 10% methanol in ethyl acetate (200 ml)
  5. concentrationThe filtrate is concentrated to oil
  6. customThe crude is purified by column chromatography (20% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-93ad0b76c3074355bb1ac967c53cf024
출처 데이터셋
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07439249B2

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