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

HRID 1950712노트

반응식

HRID 1950712 반응식
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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 702Ethanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-00b36cf1d51f47d58fff69e9d7adcd6a
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404649B2

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