Butyl Acrylate → butyl (E)-3-{3-chloro-5-methyl-4-[(5-nitropyridin-2-yl)oxy]phenyl}prop-2-enoate

HRID 1023354노트

반응식

HRID 1023354 반응식
Br[C:2]1[CH:17]=[C:16]([CH3:18])[C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][N:8]=2)=[C:4]([Cl:19])[CH:3]=1.[C:20]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])(=[O:23])[CH:21]=[CH2:22].C1(CNCC2CCCCC2)CCCCC1.F[B-](F)(F)F.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>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].O.O1CCOCC1>[Cl:19][C:4]1[CH:3]=[C:2](/[CH:22]=[CH:21]/[C:20]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:23])[CH:17]=[C:16]([CH3:18])[C:5]=1[O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][N:8]=1

참가 물질

8

반응물 4

HCID 8846Butyl AcrylateHCID 4594378Bis(cyclohexylmethyl)amineHCID 44558591Tri-t-butylphosphine fluoroborateHCID 673279772-(4-Bromo-2-chloro-6-methylphenoxy)-5-nitropyridine

생성물 1

HCID 86673386butyl (E)-3-{3-chloro-5-methyl-4-[(5-nitropyridin-2-yl)oxy]phenyl}prop-2-enoate

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

To a 1,4-dioxane (10 mL) solution of 2-(4-bromo-2-chloro-6-methylphenoxy)-5-nitropyridine (1.00 g) and butyl acrylate (0.480 mL) were added N,N-dicyclohexylmethylamine (0.655 mL), tri-tert-butylphosphine tetrafluoroborate (34 mg) and tris(dibenzylideneacetone)dipalladium (0) (40 mg) at room temperature. The resultant mixture was stirred at 70° C. under a nitrogen atmosphere for 4 hours. To the reaction mixture was added water, and extracted with AcOEt. The organic layer was washed with saturated aqueous NaCl, dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=9/1 to 1/1) to afford butyl (E)-3-{3-chloro-5-methyl-4-[(5-nitropyridin-2-yl)oxy]phenyl}prop-2-enoate as a yellow powder (1.05 g).

후처리

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with saturated aqueous NaCl
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=9/1 to 1/1)

출처 및 근거

ORD 기록
ord-79311348b70c47f6bd0f45b6b12a9c89
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722663B2

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