Toluene → (E)-methyl 4-styryl-1-naphthoate

HRID 1950712ノート

反応式

HRID 1950712 の反応式
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[C:23]1(/[CH:29]=[CH:30]/B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)(O)[O-].[Na+]>C(O)C.CCOC(C)=O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:30](/[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1)=[CH:29]\[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

9

反応物 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 5702628Styrylboronic acidHCID 22711886Methyl 4-bromo-1-naphthoate

生成物 1

HCID 66824254(E)-methyl 4-styryl-1-naphthoate

試薬・触媒・溶媒 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of methyl 4-bromo-1-naphthoate, (Preparation 1, 5.4 g, 20.4 mmol) in ethanol (50 mL) and toluene (50 mL) was added Pd(dppf)2Cl2 (760 mg, 1.0 mmol), trans-2-phenylvinylboronic acid (3.3 g, 22.4 mmol) and sodium bicarbonate aqueous solution (40 mL of 2M solution). The mixture was heated to reflux for 3 hours. The mixture was cooled to room temperature and diluted with EtOAc (150 mL) and water (75 mL). The organic phase was separated, washed with brine (50 mL), dried over sodium sulfate, and concentrated. The residue was purified by chromatography on silica gel eluting from 10:90 EtOAc:heptane to 50:50 EtOAc:heptane to afford an oil which solidified upon standing (5.3 g, 90%).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe organic phase was separated
  4. washwashed with brine (50 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel eluting from 10:90 EtOAc
  8. customheptane to 50:50 EtOAc:heptane to afford an oil which

出典と根拠

ORDレコード
ord-00b36cf1d51f47d58fff69e9d7adcd6a
出典データセット
uspto-grants-2013_03
特許番号
US08404649B2

反応ノート

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