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

HRID 1466013노트

반응식

HRID 1466013 반응식
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

참가 물질

5

반응물 2

HCID 6228DimethylformamideHCID 40596895-Bromo-2-tetralone

생성물 1

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

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178527696HCID 178527696, 화합물촉매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-51e7c770ad784dcda345adcfb2ef3087
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999990B2

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