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Imidazole → (3-(tert-Butyl-dimethyl-silanyloxy)-prop-1-ynyl]-4,5,6,7-tetrahydro-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 1473247
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HRID 1473247 반응식
[OH:1][CH2:2][C:3]#[C:4][C:5]1[C:6]2[CH2:17][CH2:16][CH2:15][CH2:14][C:7]=2[S:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11].N1C=CN=C1.[CH3:23][C:24]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])[CH3:25].CCOC(C)=O>ClCCl>[CH3:13][O:12][C:10]([C:9]1[S:8][C:7]2[CH2:14][CH2:15][CH2:16][CH2:17][C:6]=2[C:5]=1[C:4]#[C:3][CH2:2][O:1][Si:27]([C:24]([CH3:26])([CH3:25])[CH3:23])([CH3:29])[CH3:28])=[O:11]
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참가 물질

6

반응물 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 89463106Methyl 3-(3-hydroxyprop-1-yn-1-yl)-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylate

생성물 1

HCID 89462605(3-(tert-Butyl-dimethyl-silanyloxy)-prop-1-ynyl]-4,5,6,7-tetrahydro-benzo[b]thiophene-2-carboxylic acid methyl ester수율 96%

시약·촉매·용매

1
HCID 6344Dichloromethane용매

실험 절차

To a solution of methyl 3-(3-hydroxyprop-1-yn-1-yl)-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylate (8.5 g, 34 mmol) in Dichloromethane (DCM) (50 mL) was added 1H-imidazole (5.8 g, 85 mmol) and TBSCl (7.7 g, 50.9 mmol). The mixture was stirred at room temperature for 2 h. The reaction mixture was washed with water, brine, dried over Na2SO4 and concentrated to dryness. The residue was purified by chromatography column on silica gel chromatography eluted with PE:EtOAc=50:1˜20:1 to afford title product (11.9 g, 96% yield). 1HNMR: (400 MHz, CDCl3) δ 0.161 (s, 6H), 0.929 (s, 9H), 1.79-1.85 (m, 4H), 2.60-2.63 (m, 2H), 2.72-2.75 (m, 2H), 3.85 (s, 3H), 4.62 (s, 2H).

후처리

  1. washThe reaction mixture was washed with water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by chromatography column on silica gel chromatography
  5. washeluted with PE

출처 및 근거

ORD 기록
ord-f2dcd186d6d242cfa5a3e2b9b1b6d441
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09012642B2

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