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

HRID 1466013ノート

反応式

HRID 1466013 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>[Pd].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 178527696HCID 178527696、化合物触媒

実験手順

To a 20 mL microwave tube was added 5-bromo-2-tetralone (2.0 g, 8.9 mmol) and Palladium(0) Tetrakis (0.616 g, 0.533 mmol), zinc cyanide (1.0 g, 8.9 mmol), and DMF (8 mL). The tube was sealed, degassed and microwaved at 80° C. for 1.0 hour. TLC showed no starting material left. The mixture was diluted with ethyl acetate, washed with ammonium hydroxide (2M, 2 x), dried with sodium sulfate, filtered and evaporated under reduced pressure. The product was purified by silica gel chromatography with isocratic 30% ethyl acetate-hexane to furnish the title compound. 1H-NMR (500 MHz, CDCl3) δ ppm 7.57 (s, 1H), 7.55 (d, J=7.8 Hz, 1H), 7.28 (d, J=7.8 Hz, 1H), 3.67 (s, 2H), 3.14 (t, J=7.0 Hz, 2H), 2.60 (t, J=7.0 Hz, 2H).

後処理

  1. customThe tube was sealed
  2. customdegassed
  3. custommicrowaved at 80° C. for 1.0 hour
  4. waitleft
  5. additionThe mixture was diluted with ethyl acetate
  6. washwashed with ammonium hydroxide (2M, 2 x)
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe product was purified by silica gel chromatography with isocratic 30% ethyl acetate-hexane

出典と根拠

ORDレコード
ord-51e7c770ad784dcda345adcfb2ef3087
出典データセット
uspto-grants-2015_04
特許番号
US08999990B2

反応ノート

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