beta-Cyclocitral → HCID 89602863, 화합물

HRID 530234

반응식

HRID 530234 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1.C([Li])CCC.[CH3:17][C:18]1[CH2:23][CH2:22][CH2:21][C:20]([CH3:25])([CH3:24])[C:19]=1[CH:26]=[O:27]>O1CCCC1>[CH:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([CH:26]([C:19]3[C:20]([CH3:25])([CH3:24])[CH2:21][CH2:22][CH2:23][C:18]=3[CH3:17])[OH:27])[CH:11]=2)[CH:6]=[CH:7][N:8]=1

참가 물질

5

반응물 3

HCID 9895beta-CyclocitralHCID 122574417-BromoisoquinolineHCID 178418339Butyllithium

생성물 1

HCID 89602863HCID 89602863, 화합물수율 122.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

A solution of 7-bromoisoquinoline (958 mg, 4.6 mmol) in tetrahydrofuran (15 mL) was added dropwise into n-butyl lithium (1.6 M in hexane, 2.87 mL, 4.6 mmol) at −78° C. and stirred at −78° C. for 30 minutes. Then 2,6,6-trimethylcyclohex-1-enecarbaldehyde (350 mg, 2.3 mmol) in tetrahydrofuran (2 mL) was added and the reaction was stirred at −78° C. for 1 hour and then allowed to warm to room temperature. The reaction was quenched with saturated aqueous ammonium chloride and the organics were extracted with ethyl acetate. The organic phase was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (794 mg, Yield: 100%). Rf 0.5 (2:1 petroleum ether/ethyl acetate); 1H NMR (400 MHz, CDCl3) δ 9.24 (s, 1H), 8.49 (d, J=5.6 Hz, 1H), 8.04 (s, 1H), 7.78 (s, 2H), 7.64 (d, J=5.6 Hz, 1H), 5.56 (s, 1H), 2.05-2.00 (m, 2H), 1.70-1.56 (m, 4H), 1.35 (s, 3H), 1.24 (s, 3H), 1.16 (s, 3H) ppm; Mass spectrum (ESI +ve) m/z 282 (M+H+).

후처리

  1. stirringthe reaction was stirred at −78° C. for 1 hour
  2. temperatureto warm to room temperature
  3. customThe reaction was quenched with saturated aqueous ammonium chloride
  4. extractionthe organics were extracted with ethyl acetate
  5. washThe organic phase was washed with saturated aqueous sodium bicarbonate and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-3529ede6973243d5b5e40f138e3825fb
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353063B2

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