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Hydrochloric Acid → Ethyl[4-({3-[3-phenyl-8-(trifluoromethyl)quinolin-yl]phenoxy}methyl)phenyl]acetate

HRID 2104608
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HRID 2104608 반응식
[C:1]1([C:7]2[CH:8]=[N:9][C:10]3[C:15]([C:16]=2C2C=C(O)C=CC=2)=[CH:14][CH:13]=[CH:12][C:11]=3[C:24]([F:27])([F:26])[F:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:28](=[O:31])([O-])[O-].[K+].[K+].[CH2:34]([O:36][C:37](=[O:47])[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([CH2:45]Br)=[CH:41][CH:40]=1)[CH3:35].Cl>CN(C=O)C>[CH2:34]([O:36][C:37](=[O:47])[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([CH2:45][O:31][C:28]2[CH:5]=[CH:6][CH:1]=[C:2]([C:8]3[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:16][C:15]4[C:10](=[C:11]([C:24]([F:27])([F:26])[F:25])[CH:12]=[CH:13][CH:14]=4)[N:9]=3)[CH:3]=2)=[CH:41][CH:40]=1)[CH3:35]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 15712209Ethyl 2-(4-(bromomethyl)phenyl)acetateHCID 665862923-(3-Phenyl-8-trifluoromethyl-quinolin-4-yl)-phenol

생성물 1

HCID 131727587Ethyl[4-({3-[3-phenyl-8-(trifluoromethyl)quinolin-yl]phenoxy}methyl)phenyl]acetate수율 38.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-[3-phenyl-8-(trifluoromethyl)quinolin-4-yl]phenol (0.178 g, 0.487 mmol), and potassium carbonate (0.134 g, 0.974 mmol), in DMF at 120° C. is added 4-bromomethylphenylacetic acid ethyl ester (0.334 g, 1.46 mmol), drop wise over 2 h. After an additional 2 h, the cooled reaction is poured into 2N aq HCl and extracted with ethyl acetate. The combined extracts are washed with sat aq NaHCO3, water, brine, and dried with magnesium sulfate. The extracts are concentrated and the residue is chromatographed with 1:9 ethyl acetate:hexanes to afford the title compound as a syrup (0.051 g, 37%). MS m/z 542; HRMS: calcd for C33H26NF3O3+H, 542.19430; found (ESI, [M+H]+), 542.194.

후처리

  1. waitAfter an additional 2 h
  2. customthe cooled reaction
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts are washed with sat aq NaHCO3, water, brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationThe extracts are concentrated
  7. customthe residue is chromatographed with 1:9 ethyl acetate

출처 및 근거

ORD 기록
ord-a63aeddca4254a6388a9235a4eb163c2
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07576215B2

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