Triphenylphosphine → 5-(3-Nitro-phenoxy)-pentylamine

HRID 217666ノート

反応式

HRID 217666 の反応式
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[N+:16]([C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][NH2:1])([O-:18])=[O:17]

参加物

5

反応物 2

HCID 11776TriphenylphosphineHCID 866252691-(5-Azido-pentyloxy)-3-nitro-benzene

生成物 1

HCID 690096135-(3-Nitro-phenoxy)-pentylamine収率 98.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-(5-azido-pentyloxy)-3-nitro-benzene (3.12 g, 12.5 mmol) in 50 mL THF and 1 mL H2O was added triphenylphosphine (3.27 g, 12.5 mmol). The reaction mixture was stirred at room temperature for 48 hours and then was partitioned with ethyl acetate and water. The aqueous solution was extracted with ethyl acetate (3×50 mL). The combined organic phases were washed with brine, dried over MgSO4, and concentrated to give a yellow liquid, which was purified by silica gel column chromatography to give 5-(3-nitro-phenoxy)-pentylamine (2.75 g, 12.3 mmol, 98%) as a yellow liquid.

後処理

  1. customwas partitioned with ethyl acetate and water
  2. extractionThe aqueous solution was extracted with ethyl acetate (3×50 mL)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give a yellow liquid, which
  7. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-a1ee6c77ed174b35ba0cfdc90d934db9
出典データセット
uspto-grants-2012_06
特許番号
US08198284B2

反応ノート

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