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

HRID 1959615Notes

Reaction equation

HRID 1959615 reaction equation
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

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 86645365HCID 86645365, compoundHCID 178418689HCID 178418689, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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+].

Workup

  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)

Sources & evidence

ORD record
ord-4a43367ca800466080beec120ffa5227
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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