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Triphenylphosphine → 5-[4-(1-Methyl-7-azaindol-2-ylmethoxy)-benzyl]-3-triphenylmethylthiazolidine-2,4-dione

HRID 55524
ノート
印刷プレビュー

反応式

HRID 55524 の反応式
[OH:1][CH2:2][C:3]1[N:4]([CH3:12])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][N:6]=2.O[C:14]1[CH:46]=[CH:45][C:17]([CH2:18][CH:19]2[S:23][C:22](=[O:24])[N:21]([C:25]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]2=[O:44])=[CH:16][CH:15]=1.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:12][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][N:6]=2)[CH:11]=[C:3]1[CH2:2][O:1][C:14]1[CH:46]=[CH:45][C:17]([CH2:18][CH:19]2[S:23][C:22](=[O:24])[N:21]([C:25]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]2=[O:44])=[CH:16][CH:15]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 28181265-(4-Hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dioneHCID 23298289{1-methyl-1H-pyrrolo[2,3-b]pyridin-2-yl}methanol

生成物 1

HCID 232982875-[4-(1-Methyl-7-azaindol-2-ylmethoxy)-benzyl]-3-triphenylmethylthiazolidine-2,4-dione収率 71.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 103 mg of 2-hydroxymethyl-1-methyl-7-azaindole (prepared as described in Preparation 81), 346 mg of 5-(4-hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione, 166 mg of diethyl azodicarboxylate and 250 mg of triphenylphosphine in 3 ml of tetrahydrofuran was stirred at room temperature for 15 hours. At the end of this time, the reaction mixture was freed from the solvent by distillation. The resulting residue was purified by column chromatography through silica gel, using a gradient elution method, with mixtures of hexane and ethyl acetate in ratios ranging from 5:1 to 4:1 by volume as the eluent, to give 277 mg of the title compound having Rf=0.41 (on silica gel thin layer chromatography using a 1:1 by volume mixture of hexane and ethyl acetate as the developing solvent).

後処理

  1. distillationAt the end of this time, the reaction mixture was freed from the solvent by distillation
  2. customThe resulting residue was purified by column chromatography through silica gel
  3. washa gradient elution method

出典と根拠

ORDレコード
ord-17d32547514448a5af4fdb3118f1a9f1
出典データセット
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05624935

反応ノート

読み込み中…

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