Styrene → Methyl-phenyl-carbamic acid 4-styryl-phenyl ester

HRID 1180033

反応式

HRID 1180033 の反応式
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CN(C1CCCCC1)C1CCCCC1.I[C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31](=[O:40])[N:32]([CH3:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:26][CH:25]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH:1]([C:24]1[CH:25]=[CH:26][C:27]([O:30][C:31](=[O:40])[N:32]([CH3:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:28][CH:29]=1)=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

6

反応物 3

HCID 7501StyreneHCID 24210N-Methyl dicyclohexylamineHCID 69517304Methyl-phenyl-carbamic Acid 4-iodo-phenyl Ester

生成物 1

HCID 69517626Methyl-phenyl-carbamic acid 4-styryl-phenyl ester収率 17%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 178418851HCID 178418851、化合物触媒

反応条件

温度
70 °C

実験手順

Styrene (1.2 mmol), N-methyldicyclohexylamine (1.2 mmol), Pd2(dba)3 (0.03 mmol), Pd(P(t-Bu)3)2 (0.06 mmol) and methyl-phenyl-carbamic acid 4-iodo-phenyl ester (1.0 mmol) were added to a Schlenk tube under nitrogen. The Schlenk tube was evacuated and refilled with nitrogen five times. Then dioxane (2 mL) was added and the reaction mixture was stirred at 70° C. for 8 h. The crude product was purified by flash chromatography (Quad flash 12, EtOAc-heptane) giving the title compound in 17% yield as colorless crystals.

後処理

  1. customThe Schlenk tube was evacuated
  2. additionrefilled with nitrogen five times
  3. additionThen dioxane (2 mL) was added
  4. customThe crude product was purified by flash chromatography (Quad flash 12, EtOAc-heptane)

出典と根拠

ORDレコード
ord-9735057113d34874a60dc68dbff4d059
出典データセット
uspto-grants-2007_10
特許番号
US07279470B2

関連ノート

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