Sodium Bicarbonate → 1-[4-Chloro-3-(tetrahydro-pyran-2-yloxymethyl)-pyridin-2-yl]-ethanol

HRID 1959615ノート

反応式

HRID 1959615 の反応式
C[Mg+].[Br-].[Cl:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH:11]=[O:12])[C:6]=1[CH2:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1.[C:21]([O-])(O)=O.[Na+]>C1COCC1>[Cl:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH:11]([OH:12])[CH3:21])[C:6]=1[CH2:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 86645365HCID 86645365、化合物HCID 178418689HCID 178418689、化合物

生成物 1

HCID 670772151-[4-Chloro-3-(tetrahydro-pyran-2-yloxymethyl)-pyridin-2-yl]-ethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

MeMgBr (3.0 M in Diethylether. 582 μL. 1.75 mmol) was added to a stirred solution of 4-Chloro-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine-2-carbaldehyde (149 mg. 0.58 mmol) in THF (6 mL). After stirring for 10 min at room temperature sat. NaHCO3 solution (30 mL) was added and extracted three times with DCM (50 mL). The combined organic layers were dried over Na2SO4 filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with a gradient of ethyl acetate and MeOH) to give the title compound. MS (m/z): 271.8 [M+H+].

後処理

  1. additionwas added
  2. extractionextracted three times with DCM (50 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (
  7. washelution with a gradient of ethyl acetate and MeOH)

出典と根拠

ORDレコード
ord-4a43367ca800466080beec120ffa5227
出典データセット
uspto-grants-2013_04
特許番号
US08410134B2

反応ノート

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