Sodium Hydroxide → 3-(3-Quinolyl)-2-propyn-1-ol t-butyl carbonate

HRID 1370013

반응식

HRID 1370013 반응식
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]#[C:12][CH2:13][OH:14])[CH:2]=1.[C:15]([O:22]C(OC(C)(C)C)=O)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].[OH-].[Na+]>O.C(Cl)Cl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]#[C:12][CH2:13][OH:14])[CH:2]=1.[C:18]([O:17][C:15](=[O:16])[O-:22])([CH3:21])([CH3:20])[CH3:19]

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 6501423-Quinolin-3-ylprop-2-yn-1-ol

생성물 1

HCID 1317233963-(3-Quinolyl)-2-propyn-1-ol t-butyl carbonate

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

To a dry 1-L three-necked round-bottom flask equipped with a nitrogen inlet and overhead stirrer was charged 3-(3-quinolyl)-2-propyn-1-ol (15.81 g, 86.39 mmol), di-tert-butyl dicarbonate (22.48 g, 103 mmol, 1.19 equiv), n-tetrabutyl ammonium hydrogen sulfate (0.86 g, 2.54 mmol, 0.029 equiv) and methylene chloride (300 mL). The resulting suspension was mechanically stirred while a 25% w/w aqueous NaOH solution (38 g) was added in over a period of 5 minutes. The biphasic mixture which resulted was stirred for 4 hours after which time the reaction was found to be complete by HPLC and TLC. The mixture was diluted with water (200 mL) and methylene chloride (100 mL). After stirring for 10 minutes and settling for 15 minutes the layers were separated. The organic layer was washed with water (1×200 mL) and 20% aq., NaCl (1×200 mL). The organic was then stirred with 15 g of sodium sulfate, filtered and then stripped to an oil under reduced pressure. The residual oil was taken up in isopropyl acetate/ hexane (1:1, 100 mL) and passed through a small pad of silica gel (8 g). The pad was rinsed with the same eluent (100 mL). The combined filtrates were concentrated under reduced pressure and rigorously dried in a vacuum oven to yield the 3-(3-quinolyl)-2-propyn-1ol t-butyl carbonate as a light orange-yellow colored oil: 24.50 g, 100%.

후처리

  1. additionwas added in over a period of 5 minutes
  2. customThe biphasic mixture which resulted
  3. stirringAfter stirring for 10 minutes
  4. waitsettling for 15 minutes
  5. customthe layers were separated
  6. washThe organic layer was washed with water (1×200 mL) and 20% aq.
  7. stirringThe organic was then stirred with 15 g of sodium sulfate
  8. filtrationfiltered
  9. washThe pad was rinsed with the same eluent (100 mL)
  10. concentrationThe combined filtrates were concentrated under reduced pressure
  11. customrigorously dried in a vacuum oven

출처 및 근거

ORD 기록
ord-56a7c96508924bae84d6c02891d6bc94
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06579986B2

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