Sodium Hydroxide → 2-(4-Fluorophenylmethoxymethyl)thiophene

HRID 52185

반응식

HRID 52185 반응식
[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

참가 물질

7

반응물 3

HCID 14798Sodium HydroxideHCID 680214-Fluorobenzyl bromideHCID 694672-Thiophenemethanol

생성물 1

HCID 199633152-(4-Fluorophenylmethoxymethyl)thiophene수율 86%

시약·촉매·용매 3

HCID 5963Benzyltrimethylammonium chloride촉매HCID 679Dimethyl Sulfoxide용매HCID 57417360Sodium chloride; water용매

실험 절차

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% ).

후처리

  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

출처 및 근거

ORD 기록
ord-7211a6dbcfe0433eae7be03d10f925a4
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616596

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