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

HRID 1831409

Reaction equation

HRID 1831409 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 178418851HCID 178418851, compoundCatalyst

Conditions

Temperature
70 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-49393bbb9461493097fe5b44df1672b2
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Linked notes

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