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

HRID 1959615노트

반응식

HRID 1959615 반응식
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

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 86645365HCID 86645365, 화합물HCID 178418689HCID 178418689, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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+].

후처리

  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)

출처 및 근거

ORD 기록
ord-4a43367ca800466080beec120ffa5227
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410134B2

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