Aluminium lithium hydride → 4-(2-((4-Bromophenyl)amino)ethoxy)phenol

HRID 1053570ノート

反応式

HRID 1053570 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)[CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=2)=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 43326296N-(4-bromophenyl)-2-(4-hydroxyphenoxy)acetamide

生成物 1

HCID 717359264-(2-((4-Bromophenyl)amino)ethoxy)phenol収率 13%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Compound 7b (80 mg, 0.25 mmol) was dissolved in THF (5 ml). LiAlH4 (30 mg, 0.5 mmol) was added portionwise and the reaction was refluxed for 6 hrs. The reaction was quenched slowly with water, 10% sodium hydroxide, and then water again. The aqueous layer was extracted with EtOAc (2×50 mL). The organic was concentrated to yield compound 7 (10 mg, 0.03 mmol, 13% yield). 1H NMR (CDCl3, 400 MHz) δ 7.29 (m, 2H), 6.80 (q, 4H), 6.56 (d, 2H), 4.81 (broad s, 1H), 4.13 (t, 2H), 3.47 (t, 2H); HRMS (ESI, positive) m/z calcd. for C14H14BrNO2 [M+H]+: 308.0286, found: 308.0261.

後処理

  1. temperaturethe reaction was refluxed for 6 hrs
  2. customThe reaction was quenched slowly with water, 10% sodium hydroxide
  3. extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
  4. concentrationThe organic was concentrated

出典と根拠

ORDレコード
ord-7dc790868e944bea8fd18ed184c78fcc
出典データセット
uspto-grants-2016_07
特許番号
US09394233B2

反応ノート

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