Tetrahydro-4H-pyran-4-one → HCID 9817415, compound

HRID 988097Notes

Reaction equation

HRID 988097 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[Li]CCCC.[O:21]1[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]1>C1COCC1>[OH:27][C:24]1([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][N:8]3[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])=[CH:4][CH:3]=2)[CH2:25][CH2:26][O:21][CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 12992938HCID 12992938, compoundHCID 178418339Butyllithium

Product 1

HCID 9817415HCID 9817415, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of compound (ii), above, (380 mg, 1.4 mmol) in THF (5 mL) at −78° C. was added n-BuLi (1 mL, 1.6 M sol. in hexane, 1.6 mmol). The mixture was stirred at −78° C. for 20 min. Tetrahydro-4H-pyran-4-one (280 mg, 2.8 mmol) dissolved in THF (1 mL) was added and the reaction mixture stirred at −78° C. for 2 hrs. The mixture was then quenched with NH4Cl (saturated) and extracted with ethyl acetate. The organic extract was washed with brine and dried over anhydrous Na2SO4. The crude residue was purified by flash chromatography to give the title product as a yellow solid (150 mg, 37% yield).

Workup

  1. additionwas added
  2. stirringthe reaction mixture stirred at −78° C. for 2 hrs
  3. customThe mixture was then quenched with NH4Cl (saturated)
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-c29dbaa852c3496b9d855a1731003885
Source dataset
uspto-grants-2003_10
Patent number
US06635639B2

Reaction notes

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