Dimethylformamide → 6-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1519481ノート

反応式

HRID 1519481 の反応式
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:12])[CH2:7]2.[CH3:13][N:14](C=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-]#N.[Zn+2].[C-]#N>[O:12]=[C:6]1[CH2:5][CH2:4][C:3]2[CH:2]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][C:8]=2[CH2:7]1

参加物

5

反応物 2

HCID 6228DimethylformamideHCID 40596895-Bromo-2-tetralone

生成物 1

HCID 162445046-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

実験手順

The 5-bromo-2 tetralone (2.0 g, 8.9 mmol), tetrakis(triphenylphosphine)palladium (0.62 g, 0.53 mmol) and zinc cyanide (0.73 g, 6.2 mmol) were added to 4 ml DMF in a 20 ml microwave tube. The mixture was degassed and microwaved at 80° C. for 30 mins. TLC showed no starting material left and the mixture was diluted with ethyl acetate and washed with ammonium hydroxide (2M, ×4 ml). The organic layer was separated and dried over Na2SO4 then filtered. The solvent was evaporated under reduced pressure. The residue was chromatographed through 40 gm Isco Redi-sep column and eluted with 0-30% ethyl acetate-hexane to yield 6-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile.

後処理

  1. customThe mixture was degassed
  2. custommicrowaved at 80° C. for 30 mins
  3. waitleft
  4. additionthe mixture was diluted with ethyl acetate
  5. washwashed with ammonium hydroxide (2M, ×4 ml)
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. filtrationthen filtered
  9. customThe solvent was evaporated under reduced pressure
  10. customThe residue was chromatographed through 40 gm Isco Redi-sep column
  11. washeluted with 0-30% ethyl acetate-hexane

出典と根拠

ORDレコード
ord-695c76498fa64d55931d4f8907676657
出典データセット
uspto-grants-2015_07
特許番号
US09073882B2

反応ノート

読み込み中…