2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 5-(Hydroxymethyl)-1'-((2-(trimethylsilyl)ethoxy)methyl)-3H-spiro[furo[2,3-b]pyridine-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 931391ノート

反応式

HRID 931391 の反応式
C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.COC1C=CC(C[O:22][CH2:23][C:24]2[CH:25]=[C:26]3[CH2:49][C:31]4([C:39]5[C:34](=[N:35][CH:36]=[CH:37][CH:38]=5)[N:33]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:47])([CH3:46])[CH3:45])[C:32]4=[O:48])[O:30][C:27]3=[N:28][CH:29]=2)=CC=1>ClCCl.O>[OH:22][CH2:23][C:24]1[CH:25]=[C:26]2[CH2:49][C:31]3([C:39]4[C:34](=[N:35][CH:36]=[CH:37][CH:38]=4)[N:33]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:45])([CH3:46])[CH3:47])[C:32]3=[O:48])[O:30][C:27]2=[N:28][CH:29]=1

参加物

5

反応物 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 900505505-(((4-Methoxybenzyl)oxy)methyl)-1'-((2-(trimethylsilyl)ethoxy)methyl)-3H-spiro[furo[2,3-b]pyridine-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

生成物 1

HCID 1317351675-(Hydroxymethyl)-1'-((2-(trimethylsilyl)ethoxy)methyl)-3H-spiro[furo[2,3-b]pyridine-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
23 °C

実験手順

DDQ (0.533 g, 2.35 mmol) was added to a solution of 5-(((4-methoxybenzyl)oxy)methyl)-1′-((2-(trimethylsilyl)ethoxy)methyl)-3H-spiro[furo[2,3-b]pyridine-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (0.61 g, 1.2 mmol) in dichloromethane (16 mL) and water (4 mL) at 0° C. The resulting mixture was gradually warmed to 23° C. and stirred for 1 h, then partitioned between saturated aqueous sodium bicarbonate solution and dichloromethane. The organic layer was dried over sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 50% ethyl acetate in petroleum ether to give the title compound as a racemic mixture. MS: m/z=400.2 (M+1).

後処理

  1. custompartitioned between saturated aqueous sodium bicarbonate solution and dichloromethane
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on silica gel eluting with 50% ethyl acetate in petroleum ether

出典と根拠

ORDレコード
ord-e493929efb204bef8e856d43851c845a
出典データセット
uspto-grants-2016_03
特許番号
US09296750B2

反応ノート

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