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

HRID 1023354ノート

反応式

HRID 1023354 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-79311348b70c47f6bd0f45b6b12a9c89
出典データセット
uspto-grants-2014_05
特許番号
US08722663B2

反応ノート

読み込み中…