4-Aminophenol → 4-(4-Trifluoromethyl-benzyloxy)-phenylamine

HRID 855991ノート

反応式

HRID 855991 の反応式
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.[F:9][C:10]([F:20])([F:19])[C:11]1[CH:18]=[CH:17][C:14]([CH2:15]O)=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(OCC)(=O)C>[F:9][C:10]([F:19])([F:20])[C:11]1[CH:18]=[CH:17][C:14]([CH2:15][O:8][C:3]2[CH:4]=[CH:5][C:6]([NH2:7])=[CH:1][CH:2]=2)=[CH:13][CH:12]=1

参加物

7

反応物 4

HCID 4034-AminophenolHCID 11776TriphenylphosphineHCID 676844-(Trifluoromethyl)benzenemethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

生成物 1

HCID 221378894-(4-Trifluoromethyl-benzyloxy)-phenylamine収率 55.6%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of p-aminophenol (0.200 g, 1.83 mmol), 4-trifluoromethylbenzyl alcohol (025 ml, 1.83 mmol) and triphenylphosphine (0.529 g, 2.02 mmol) in 5 ml anhydrous tetrahydrofuran was added diethyl azodicarboxylate (0.318 ml, 2.02 mmol). The reaction mixture was stirred overnight at room temperature under nitrogen. It was then diluted with 70 ml ethyl acetate and the resulting solution was washed sequentially with 50 ml saturated aqueous sodium bicarbonate solution, 50 ml water and 50 ml brine, dried (anhydrous sodium sulfate) and concentrated under reduced pressure. The solid residue was purified by flash column chromatography (silica gel, 15 g), eluting with 8:2 hexane/ethyl acetate to yield the title compound as an off-white solid (0.272 g, 55% yield). MS: 284.1 (M+1)

後処理

  1. washthe resulting solution was washed sequentially with 50 ml saturated aqueous sodium bicarbonate solution, 50 ml water and 50 ml brine
  2. dry with materialdried (anhydrous sodium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. customThe solid residue was purified by flash column chromatography (silica gel, 15 g)
  5. washeluting with 8:2 hexane/ethyl acetate

出典と根拠

ORDレコード
ord-461a073b170248c18ecf6d154c8e8b49
出典データセット
uspto-grants-2007_08
特許番号
US07262318B2

反応ノート

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