Tetrahydro-4H-pyran-4-one → 4-(2-Fluoropyridin-3-YL)tetrahydro-2H-pyran-4-OL

HRID 410224Notes

Reaction equation

HRID 410224 reaction equation
Br[C:2]1[C:3]([F:8])=[N:4][CH:5]=[CH:6][CH:7]=1.C([Mg]Cl)(C)C.[O:14]1[CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH2:15]1>C1COCC1>[F:8][C:3]1[C:2]([C:17]2([OH:20])[CH2:18][CH2:19][O:14][CH2:15][CH2:16]2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 27627783-Bromo-2-fluoropyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 593271844-(2-Fluoropyridin-3-YL)tetrahydro-2H-pyran-4-OL

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-2-fluoropyridine (0.93 g, 5.28 mmol) in THF (5 mL) was added dropwise isopropylmagnesium chloride (2.64 mL, 5.28 mmol, 2M solution) at room temperature. After overnight stirring, dihydro-2H-pyran-4(3H)-one (0.486 mL, 5.28 mmol) was added dropwise. Reaction was quenched with saturated NH4Cl solution and extracted with DCM. Purification by Biotage (0-10% MeOH/DCM) produced the desired product.

Workup

  1. customReaction
  2. customwas quenched with saturated NH4Cl solution
  3. extractionextracted with DCM
  4. customPurification by Biotage (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-801f3dece8d9464f846672b6e8865084
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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