Potassium Hydroxide → 1-Hydroxy-1-(perfluoroethyl)-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile

HRID 877462노트

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HRID 877462 반응식
[F:1][C:2]([F:37])([C:7]1([O:32][Si](C)(C)C)[C:19]2[N:18](S(C3C=CC(C)=CC=3)(=O)=O)[C:17]3[C:12](=[CH:13][C:14]([C:30]#[N:31])=[CH:15][CH:16]=3)[C:11]=2[CH2:10][CH2:9][CH2:8]1)[C:3]([F:6])([F:5])[F:4].[OH-].[K+]>C1COCC1.O>[OH:32][C:7]1([C:2]([F:37])([F:1])[C:3]([F:4])([F:5])[F:6])[C:19]2[NH:18][C:17]3[C:12](=[CH:13][C:14]([C:30]#[N:31])=[CH:15][CH:16]=3)[C:11]=2[CH2:10][CH2:9][CH2:8]1

참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 86676823HCID 86676823, 화합물

생성물 1

HCID 529475461-Hydroxy-1-(perfluoroethyl)-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile수율 40.4%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-(perfluoroethyl)-9-tosyl-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile (180 mg, 0.3 mmol) in THF (5 mL), KOH (90 mg, 1.6 mmol) in H2O (1 mL) was added. The reaction mixture was refluxed for 20 h, diluted with water and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to give the crude residue which was purified by column chromatography [EtOAc-hexane (1:19) as eluant] to afford the title compound as a white solid (40 mg, 40%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.5 (bs, 1H), 7.9 (s, 1H), 7.49 (d, J=7.5 Hz, 1H), 7.44 (d, J=7.5 Hz, 1H), 2.90-2.86 (m, 1H), 2.74-2.56 (m, 1H), 2.56 (s, 1H), 2.33-2.29 (m, 1H), 2.20-2.12 (m, 2H), 2.04-2.03 (m, 1H).

후처리

  1. temperatureThe reaction mixture was refluxed for 20 h
  2. extractionextracted with EtOAc (3×20 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude residue which
  6. customwas purified by column chromatography [EtOAc-hexane (1:19) as eluant]

출처 및 근거

ORD 기록
ord-df864dabd347437f95b14a08aff6b950
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987319B2

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