Hydrochloric Acid → HCID 18174370, 화합물

HRID 395330노트

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HRID 395330 반응식
II.[CH2:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:11][N:12]1[CH2:17][C:16]([C:18]([O:20][CH3:21])=[O:19])=[CH:15][CH2:14][CH2:13]1.Cl>CCOCC.C(Cl)C1C=CC=CC=1.O>[CH2:3]([CH:15]1[CH2:14][CH2:13][N:12]([CH3:11])[CH2:17][CH:16]1[C:18]([O:20][CH3:21])=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 2230ArecolineHCID 7503Benzyl Chloride3회

생성물 1

HCID 18174370HCID 18174370, 화합물

시약·촉매·용매 3

HCID 7503Benzyl Chloride촉매HCID 962Water용매HCID 3283Diethyl Ether용매5회

반응 조건

온도
-15 °C

실험 절차

To a solution of 480 mg of Mg in 2 mL of dry ether was added a little bit of I2 and several drops of benzyl chloride (about 0.5 mL) of the solution of 2.3 mL (20 mmol) of benzyl chloride in 10 mL of ether. The mixture was gentle stirred, as soon as the reaction sets in, the reminder of benzyl chloride in ether was added at the rate that the reaction went vigorously by cooling the flask with water. Then the resulting solution was stirred at gentle reflux for fifteen minutes after, all the benzyl chloride has been added. Another 5 mL of dry ether was added to the Grignard reagent solution and it was cooled to −15° C., the arecoline (1.5 g) in 20 mL of dry ether was added dropwise to it. The resulting mixture was stirred at −15° C. for another 0.5 hour. The mixture was cooled to about −40° C. and treated slowly with 10% HCl (22 mL). The aqueous layer was separated, extracted with ether (20 mL), and then basified with saturated sodium bicarbonate solution when cooled in an ice bath. The mixture was extracted with ether and the combined organic extracts were washed with brine, dried and concentrated under reduced pressure. Flash chromatography afforded a mixture of cis isomer 76 and trans isomer 77 (500 mg, 21%).

후처리

  1. additionwas added at the rate that the reaction
  2. additionhas been added
  3. stirringThe resulting mixture was stirred at −15° C. for another 0.5 hour
  4. temperatureThe mixture was cooled to about −40° C.
  5. customThe aqueous layer was separated
  6. extractionextracted with ether (20 mL)
  7. temperaturecooled in an ice bath
  8. extractionThe mixture was extracted with ether
  9. washthe combined organic extracts were washed with brine
  10. customdried
  11. concentrationconcentrated under reduced pressure
  12. customFlash chromatography afforded
  13. additiona mixture of cis

출처 및 근거

ORD 기록
ord-b7edc87489af4b42956b80a452cc82ac
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06605621B1

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