Tetrahydro-4H-pyran-4-one → HCID 59326990, compound

HRID 1880088Notes

Reaction equation

HRID 1880088 reaction equation
Br[C:2]1[C:3]([Cl: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>[Cl: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 6933243-Bromo-2-chloropyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 59326990HCID 59326990, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-2-chloropyridine (0.33 g, 1.715 mmol) in THF (2 mL) at room temperature was added isopropylmagnesium chloride (0.857 mL, 1.715 mmol, 2M solution). Reaction mixture was stirred for 1 hr at room temperature before addition of dihydro-2H-pyran-4(3H)-one (0.158 mL, 1.715 mmol). After overnight stirring, reaction mixture was quenched with saturated NH4Cl solution followed by aqueous workup. Purification by Prep-plate TLC (10% MeOH/DCM) produced product that was advanced to the next step.

Workup

  1. customReaction mixture
  2. customreaction mixture
  3. customwas quenched with saturated NH4Cl solution
  4. customPurification by Prep-plate TLC (10% MeOH/DCM)
  5. customproduced product that

Sources & evidence

ORD record
ord-e6e35e7cff4147b9b5db0258207ba600
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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