Nitrogen → 3,N,N-Trimethyl-4-vinylbenzamide

HRID 1754903ノート

反応式

HRID 1754903 の反応式
Br[C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]([CH3:10])[CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:13].[CH:14]([B-](F)(F)F)=[CH2:15].[K+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].N#N>C1COCC1.Cl[Pd]Cl.O>[CH3:13][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=1[CH:14]=[CH2:15])[C:6]([N:8]([CH3:10])[CH3:9])=[O:7]

参加物

9

反応物 5

HCID 947NitrogenHCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 189605694-bromo-N,N,3-trimethylbenzamideHCID 23679353Potassium vinyltrifluoroborate

生成物 1

HCID 668162113,N,N-Trimethyl-4-vinylbenzamide収率 90.5%

試薬・触媒・溶媒 3

HCID 24290Palladium Chloride触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 4-bromo-3,N,N-trimethyl-benzamide (798 mg, 3.30 mmol), potassium vinyltrifluoroborate (579 mg, 4.32 mmol), PdCl2 (59.0 mg, 0.333 mmol), PPh3 (265 mg, 1.01 mmol) and Cs2CO3 (3.22 g, 9.90 mmol) in THF (6.5 ml)-H2O (0.65 ml) was heated with stirring at 85° C. for 21 hours in a sealed test tube in an N2 atmosphere. The reaction mixture was cooled to room temperature and then extracted with ether. The organic layer was washed with water, and then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to give 3,N,N-trimethyl-4-vinyl-benzamide (565 mg, 90%).

後処理

  1. temperaturewas heated
  2. extractionextracted with ether
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

出典と根拠

ORDレコード
ord-b0aa6487ebc643aaa7139fa225f38a9b
出典データセット
uspto-grants-2015_10
特許番号
US09169254B2

反応ノート

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