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Imidazole → Methyl 2-(1,3-benzodioxol-5-yl)-2-[1-methyl-6-(triisopropylsilyloxymethyl)-1H-3-indolyl]acetate

HRID 381323
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HRID 381323 반응식
Cl[Si:2]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[CH:3]([CH3:5])[CH3:4].[O:12]1[C:16]2[CH:17]=[CH:18][C:19]([CH:21]([C:26]3[C:34]4[C:29](=[CH:30][C:31]([CH2:35][OH:36])=[CH:32][CH:33]=4)[N:28]([CH3:37])[CH:27]=3)[C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:15]=2[O:14][CH2:13]1.N1C=CN=C1>CN(C)C=O>[O:12]1[C:16]2[CH:17]=[CH:18][C:19]([CH:21]([C:26]3[C:34]4[C:29](=[CH:30][C:31]([CH2:35][O:36][Si:2]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[CH:3]([CH3:5])[CH3:4])=[CH:32][CH:33]=4)[N:28]([CH3:37])[CH:27]=3)[C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:15]=2[O:14][CH2:13]1
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참가 물질

5

반응물 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 22467201Methyl 2-(1,3-benzodioxol-5-yl)-2-[6-(hydroxymethyl)1-methyl-1H-3-indolyl]acetate

생성물 1

HCID 22467250Methyl 2-(1,3-benzodioxol-5-yl)-2-[1-methyl-6-(triisopropylsilyloxymethyl)-1H-3-indolyl]acetate수율 80.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

실험 절차

Chlorotriisopropylsilane (0.19 ml, 0.88 mmol) was added to a solution of methyl 2-(1,3-benzodioxol-5-yl)-2-[6-(hydroxymethyl)-1-methyl-1H-3-indolyl]acetate (from step (d), 260 mg, 0.74 mmol) and imidazole (100 mg, 1.47 mmol) in anhydrous dimethylformamide (3 ml). After 3 hours the mixture was partitioned between diethyl ether and water, the organic layer was separated and washed with water. The organic layer was dried (magnesium sulphate), and the solvent removed in vacuo. The residue was flash chromatographed (using 50% dichloromethane, 50% hexane as eluent) to give the subtitle compound (305 mg) as an oil.

후처리

  1. customAfter 3 hours the mixture was partitioned between diethyl ether and water
  2. customthe organic layer was separated
  3. washwashed with water
  4. dry with materialThe organic layer was dried (magnesium sulphate)
  5. customthe solvent removed in vacuo
  6. customchromatographed (using 50% dichloromethane, 50% hexane as eluent)

출처 및 근거

ORD 기록
ord-3ee36ad7a45542b49ffcc7e4148e0ee4
출처 데이터셋
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06306852B1

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