Triethylamine → (5-Chloro-2-neopentylamino-phenyl)-(2,3-ethylenedioxyphenyl)-methanol

HRID 1862546노트

반응식

HRID 1862546 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.B(Cl)(Cl)Cl.[CH2:18]1[CH2:29][O:28][C:27]2[C:20](=[C:21]([CH:24]=[CH:25][CH:26]=2)[CH:22]=[O:23])[O:19]1.C(N(CC)CC)C>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([CH:22]([C:21]2[CH:24]=[CH:25][CH:26]=[C:27]3[O:28][CH2:29][CH2:18][O:19][C:20]=23)[OH:23])[CH:3]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 25135Boron TrichlorideHCID 27950332,3-Dihydro-1,4-benzodioxine-5-carbaldehydeHCID 11424155(4-Chloro-phenyl)-(neopentyl)-amine

생성물 1

HCID 12045573(5-Chloro-2-neopentylamino-phenyl)-(2,3-ethylenedioxyphenyl)-methanol수율 88.5%

시약·촉매·용매 1

HCID 241Benzene용매3회

실험 절차

A solution of (4-chloro-phenyl)-(neopentyl)-amine (2.24 g, 11.3 mmol) in benzene (6 mL) was added to a solution of boron trichloride (1.0 M in xylenes; 12.5 mL, 12.5 mmol) in benzene (13 mL) at 0° C. under a nitrogen atmosphere. Once the addition was complete, the resulting mixture was heated at reflux for 3 hours, under a steady stream of nitrogen exiting into an aqueous 5N sodium hydroxide trap, and then recooled to 0° C. A solution of 2,3-ethylenedioxybenzaldehyde (1.86 g, 11.3 mmol), triethylamine (2.29 g, 22.7 mmol, 3.2 mL) and benzene (6 mL) was then added and the resulting mixture stirred 3.5 hours before quenching with aqueous 1N hydrochloric acid. After 1 hour, ethyl acetate was added and the resulting mixture was shaken vigorously. The aqueous layer was alkalized with aqueous 5N sodium hydroxide and the layers separated. The aqueous layer was extracted with ethyl acetate (2×). The organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified by flash column chromatography (4:1 hexanes/ethyl acetate) to produce 3.62 g (88%) of the title compound as an off-white foam.

후처리

  1. additionOnce the addition
  2. temperaturethe resulting mixture was heated
  3. temperatureat reflux for 3 hours, under a steady stream of nitrogen exiting into an aqueous 5N sodium hydroxide trap
  4. customrecooled to 0° C
  5. custombefore quenching with aqueous 1N hydrochloric acid
  6. waitAfter 1 hour
  7. additionethyl acetate was added
  8. stirringthe resulting mixture was shaken vigorously
  9. customthe layers separated
  10. extractionThe aqueous layer was extracted with ethyl acetate (2×)
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. custompurified by flash column chromatography (4:1 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-87f2f5667f734c7393f14ebf65792491
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06537987B1

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