Sodium hydride → 4-Fluoro-2-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-pyridine

HRID 711186

反応式

HRID 711186 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][OH:10].[H-].[Na+].F[C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][N:15]=1>C1COCC1>[F:20][C:18]1[CH:17]=[CH:16][N:15]=[C:14]([O:10][CH2:9][CH2:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[CH:19]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 27628382,4-DifluoropyridineHCID 41668332-(Oxan-2-yloxy)ethan-1-ol

生成物 1

HCID 1177296274-Fluoro-2-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-pyridine収率 52.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

2-(Tetrahydro-2H-pyran-2-yl-oxy)ethanol (731 mg, 679 μL, 5.00 mmol) was suspended in anhydrous THF and NaH (60% dispersion in mineral oil, 240 mg, 6.0 mmol) was added portionwise, resulting in evolution of gas and the reaction stirred at room temp. After 15 min, a solution of 2,4-difluoropyridine (690 mg, 6.00 mmol) in anhydrous THF (2 mL) was slowly added. After stirring for 2 h, the reaction was partitioned between H2O and EtOAc. The organic layer was separated, and the aqueous extracted again with EtOAc. The combined organics were dried over MgSO4, concentrated in vacuo and subjected to FCC, eluting with 0-30% EtOAc/cyclohexane, to afford the title compound as a colourless oil (633 mg, 43%). LCMS (Method 3) Rt 3.57 min, m/z 264.2 [M+Na].

後処理

  1. customresulting in evolution of gas
  2. stirringAfter stirring for 2 h
  3. customthe reaction was partitioned between H2O and EtOAc
  4. customThe organic layer was separated
  5. extractionthe aqueous extracted again with EtOAc
  6. dry with materialThe combined organics were dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. washeluting with 0-30% EtOAc/cyclohexane

出典と根拠

ORDレコード
ord-57615da830624819a0580ca23828a718
出典データセット
uspto-grants-2015_11
特許番号
US09181242B2

関連ノート

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