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Propargyl alcohol → 4-[3-Hydroxy-1-propynyl]phenyl 2-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl Ketone

HRID 1387061
ノート
印刷プレビュー

反応式

HRID 1387061 の反応式
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:19][C:18]4[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=4[C:16]=3[C:24]([C:26]3[CH:31]=[CH:30][C:29](I)=[CH:28][CH:27]=3)=[O:25])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:33]([OH:36])[C:34]#[CH:35].[Al]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:19][C:18]4[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=4[C:16]=3[C:24]([C:26]3[CH:31]=[CH:30][C:29]([C:35]#[C:34][CH2:33][OH:36])=[CH:28][CH:27]=3)=[O:25])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]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 3

HCID 7859Propargyl alcoholHCID 5359268AluminumHCID 211826284-Iodophenyl 2-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl Ketone

生成物 1

HCID 211829164-[3-Hydroxy-1-propynyl]phenyl 2-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl Ketone

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 178418476HCID 178418476、化合物触媒

実験手順

A solution of 4-iodophenyl 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl ketone (Part A; 5.0 g, 9.0 mmol) was treated with propargyl alcohol (1.05 mL, 18.1 mmol) and Pd(PPh3)2Cl2 (190 mg, 0.27 mmol). The reaction vessel was covered with aluminum foil to keep out light, and CuI (35 mg, 0.18 mmol) was added. After stirring overnight at ambient temperature, the reaction mixture was filtered over diatomaceous earth and concentrated in vacuo. Purification by flash chromatography (SiO2; 4% MeOH in CHCl3, saturated with NH4OH) gave 4.32 g (8.97 mmol; quantitative) of the title product as a light brown foam.

後処理

  1. additionwas added
  2. filtrationthe reaction mixture was filtered over diatomaceous earth
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography (SiO2; 4% MeOH in CHCl3, saturated with NH4OH)

出典と根拠

ORDレコード
ord-19f44bd4fb2e4859b0c23011fded9f53
出典データセット
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06265575B1

反応ノート

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