Sodium Hydroxide → 2-(4-Fluorophenylmethoxymethyl)thiophene

HRID 52185

反応式

HRID 52185 の反応式
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH2:15][OH:16].[OH-].[Na+]>CS(C)=O.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.[Cl-].[Na+].O>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:16][CH2:15][C:11]2[S:10][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 14798Sodium HydroxideHCID 680214-Fluorobenzyl bromideHCID 694672-Thiophenemethanol

生成物 1

HCID 199633152-(4-Fluorophenylmethoxymethyl)thiophene収率 86%

試薬・触媒・溶媒 3

HCID 5963Benzyltrimethylammonium chloride触媒HCID 679Dimethyl Sulfoxide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution in DMSO (30 mL) of 4-fluorobenzyl bromide (3.27 mL, 26.3 mmol), 2-thiophenemethanol (3.00 mL, 31.7 mmol), and benzyltrimethylammonium chloride (244 mg, 1.31 mmol) was added NaOH (6.31 g, 159 mmol) and the reaction mixture was stirred for 17 hours at ambient temperature. The reaction mixture was poured into brine and extracted with ether. The organic phase was washed with 1N aqueous H3PO4 (3×), H2O (3×), saturated aqueous NaHCO3 (2×), and brine, dried over MgSO4, filtered, and concentrated in vacuo. Chromatography on silica gel (20% ethyl acetate/hexane) gave 2-(4-fluorophenylmethoxymethyl)thiophene (5.03 g, 86% ).

後処理

  1. extractionextracted with ether
  2. washThe organic phase was washed with 1N aqueous H3PO4 (3×), H2O (3×), saturated aqueous NaHCO3 (2×), and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7211a6dbcfe0433eae7be03d10f925a4
出典データセット
uspto-grants-1997_04
特許番号
US05616596

関連ノート

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