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

HRID 381323
ノート
印刷プレビュー

反応式

HRID 381323 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3ee36ad7a45542b49ffcc7e4148e0ee4
出典データセット
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06306852B1

反応ノート

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