Potassium Hydroxide → 6-((Tetrahydro-2H-pyran-4-yl)methoxy)-5-(trifluoromethyl)picolinic acid

HRID 927671

反応式

HRID 927671 の反応式
Cl[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[OH-].[K+].[O:17]1[CH2:22][CH2:21][CH:20]([CH2:23][OH:24])[CH2:19][CH2:18]1>CS(C)=O>[O:17]1[CH2:22][CH2:21][CH:20]([CH2:23][O:24][C:2]2[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=2[C:11]([F:14])([F:13])[F:12])[CH2:19][CH2:18]1

参加物

5

反応物 3

HCID 14797Potassium HydroxideHCID 2773573(Oxan-4-yl)methanolHCID 707010166-Chloro-5-(trifluoromethyl)picolinic acid

生成物 1

HCID 710873886-((Tetrahydro-2H-pyran-4-yl)methoxy)-5-(trifluoromethyl)picolinic acid収率 86.4%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

6-Chloro-5-(trifluoromethyl)picolinic acid (330 mg, 1.46 mmol) and powdered potassium hydroxide (328 mg, 5.85 mmol) were dissolved in DMSO (9 mL). The solution was stirred for 15 min. at ambient temperature. (Tetrahydro-2H-pyran-4-yl)methanol (170 mg, 170 μL, 1.46 mmol; CAN 14774-37-9) was added. The mixture was stirred for 1 d at ambient temp., poured onto ice water/brine/1N HCl (75 mL) and extracted with EtOAc (2×150 mL). The combined extracts were washed with ice water/brine (75 mL), dried over Na2SO4. The solvent was removed under reduced pressure to give the title compound as a grey solid (385 mg, 86%) which was used in the next step without further purification. MS: 304.0 [M−H]−.

後処理

  1. stirringThe mixture was stirred for 1 d at ambient temp.
  2. additionpoured onto ice water/brine/1N HCl (75 mL)
  3. extractionextracted with EtOAc (2×150 mL)
  4. washThe combined extracts were washed with ice water/brine (75 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-666749d2019940a580444638bd298caa
出典データセット
uspto-grants-2016_03
特許番号
US09290451B2

関連ノート

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