3,4-dihydro-2H-pyran → 2-(4-bromo-3-fluoro-5-((tetrahydro-2H-pyran-2-yloxy)methyl)phenoxy)tetrahydro-2H-pyran

HRID 1020795ノート

反応式

HRID 1020795 の反応式
[Br:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][C:5]([OH:10])=[CH:4][C:3]=1[F:11].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1>ClCCl.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O>[Br:1][C:2]1[C:7]([CH2:8][O:9][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)=[CH:6][C:5]([O:10][CH:17]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[CH:4][C:3]=1[F:11]

参加物

5

反応物 2

HCID 80803,4-dihydro-2H-pyranHCID 667266582-Bromo-3-fluoro-5-hydroxybenzyl alcohol

生成物 1

HCID 667261942-(4-bromo-3-fluoro-5-((tetrahydro-2H-pyran-2-yloxy)methyl)phenoxy)tetrahydro-2H-pyran収率 92.1%

試薬・触媒・溶媒 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 4-bromo-3-fluoro-5-(hydroxymethyl)phenol (5.64 g, 25.5 mmol), 3,4-dihydro-2H-pyran (5.8 mL, 64 mmol), and dl-camphorsulfonic acid (118 mg, 2 mol %) in dichloromethane (150 mL) was stirred at room temperature for overnight. The mixture was washed with saturated aqueous sodium bicarbonate and brine, and dried on anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by silica gel chromatography (9:1 hexane/ethyl acetate) to give 2-(4-bromo-3-fluoro-5-((tetrahydro-2H-pyran-2-yloxy)methyl)phenoxy)tetrahydro-2H-pyran (9.14 g, 92%).

後処理

  1. washThe mixture was washed with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried on anhydrous sodium sulfate
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by silica gel chromatography (9:1 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-e0016dcd3b804ad5947d97beee685d82
出典データセット
uspto-grants-2014_05
特許番号
US08716478B2

反応ノート

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