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

HRID 2284473ノート

反応式

HRID 2284473 の反応式
[Br:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][C:5]([OH:10])=[C:4]([F:11])[CH:3]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1>C(Cl)Cl.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=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)=[C:4]([F:11])[CH:3]=1

参加物

5

反応物 2

HCID 80803,4-dihydro-2H-pyranHCID 667264354-Bromo-2-fluoro-5-(hydroxymethyl)phenol2 回

生成物 1

HCID 667266902-(4-bromo-2-fluoro-5-((tetrahydro-2H-pyran-2-yloxy)methyl)phenoxy)tetrahydro-2H-pyran収率 83%

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

Protection of the alcohol was carried out by making a solution of 4-bromo-2-fluoro-5-(hydroxymethyl)phenol (1.37 g, 6.19 mmol), 3,4 dihydro-2H-pyran (1.4 mL, 15 mmol) in 20 mL of CH2Cl2. The reaction mixture was then treated with camphor sulfonic acid (58 mg, 0.25 mmol) before stirring at room temperature for 21 hr. The reaction mixture was then quenched with equal volumes of 0.2 M NaOH and EtOAc (1:1, 20 mL) before the layers were separated. The water phase was further extracted with equal volume of EtOAc before the organic layers were combined and dried over anhydrous Na2SO4 and filtered. The solvent was removed under reduced pressure. The residue was purified by silica gel column using Combiflash to give 2-(4-bromo-2-fluoro-5-((tetrahydro-2H-pyran-2-yloxy)methyl)phenoxy)tetrahydro-2H-pyran (2.0 g, 83%).

後処理

  1. customThe reaction mixture was then quenched with equal volumes of 0.2 M NaOH and EtOAc (1:1, 20 mL) before the layers
  2. customwere separated
  3. extractionThe water phase was further extracted with equal volume of EtOAc before the organic layers
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column

出典と根拠

ORDレコード
ord-3016616cd68c4ee29ccd2a8ad7dd5112
出典データセット
uspto-grants-2015_09
特許番号
US09145429B2

反応ノート

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