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

HRID 1519481노트

반응식

HRID 1519481 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>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 178418397HCID 178418397, 화합물촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-695c76498fa64d55931d4f8907676657
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073882B2

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