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

HRID 1180033

반응식

HRID 1180033 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 69517626Methyl-phenyl-carbamic acid 4-styryl-phenyl ester수율 17%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 178418851HCID 178418851, 화합물촉매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9735057113d34874a60dc68dbff4d059
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279470B2

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