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

HRID 2104608
ノート
印刷プレビュー

反応式

HRID 2104608 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a63aeddca4254a6388a9235a4eb163c2
出典データセット
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07576215B2

反応ノート

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