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Water → HCID 10116596, 화합물

HRID 1633450
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HRID 1633450 반응식
[CH2:1]([N:8]1[CH2:21][CH2:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]4[O:25][CH2:24][CH:23]=[CH:22][C:17]4=3)[NH:12][C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[O:28]([CH2:35][CH2:36][CH2:37][CH2:38]Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:21][CH2:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]4[O:25][CH2:24][CH:23]=[CH:22][C:17]4=3)[N:12]([CH2:38][CH2:37][CH2:36][CH2:35][O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 70986(4-Bromobutoxy)benzeneHCID 9862338HCID 9862338, 화합물

생성물 1

HCID 10116596HCID 10116596, 화합물수율 29%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 8857
Ethyl Acetate
용매

실험 절차

To a solution containing the compound of Example 3 (0.08 g., 0.24 mmol) in N,N-dimethylformamide (5.00 mL) was added sodium hydride (0.011 g., 60% in oil, 0.29 mmol) at 0° C. The mixture was stirred at room temperature for 20 minutes, then cooled to 0° C. 4-Phenoxybutyl bromide (0.072 g., 0.32 mmol) was added to the mixture, the resulting mixture was stirred at room temperature for 16 hours. Water and ethyl acetate then were added to the mixture, and the organic and aqueous phases were separated. The aqueous layer then was extracted with ethyl acetate (2×). The combined ethyl acetate solution was dried (MgSO4) and filtered. The filtrate was concentrated in vacuo. The residue was subjected to preparative thin layer chromatography (silica gel, 50% EtOAc/hexane) to yield the alkylated compound (0.033 g, 29%) as a light yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.42, 7.13, 7.03, 6.95, 6.87, 6.71, 5.81, 4.69-4.67, 4.09, 3.93, 3.75, 3.17-3.14, 2.97-2.94, 1.87-1.76; MS (ESI+) m/z 479 (M++1).

후처리

  1. temperaturecooled to 0° C
  2. stirringthe resulting mixture was stirred at room temperature for 16 hours
  3. customthe organic and aqueous phases were separated
  4. extractionThe aqueous layer then was extracted with ethyl acetate (2×)
  5. dry with materialThe combined ethyl acetate solution was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-60c96e541ffd49828713121b8ae6bfeb
출처 데이터셋
uspto-grants-2003_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06503899B2

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