Acetone → HCID 59636235, compound

HRID 2383947Notes

Reaction equation

HRID 2383947 reaction equation
C([Li])CCC.[Br:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[CH3:13][C:14]([CH3:16])=[O:15].C(OC(=O)C)C>C1COCC1.CCCCCC>[Br:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[C:14]([OH:15])([CH3:16])[CH3:13]

Participants

7

Reactant 4

HCID 180AcetoneHCID 8857Ethyl AcetateHCID 122863-BromopyridineHCID 178418339Butyllithium

Product 1

HCID 59636235HCID 59636235, compoundYield 41.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
-10 °C

Procedure

n-Butyl Lithium (10.28 mL, 16.455 mmol) was added to a solution of DIPA (2.66 mL, 18.98 mmol) in THF (25 mL) at -78° C. The reaction mixture was stirred at -10° C. for 10 mins, followed by the addition of 3-bromo-pyridine (500 mg, 2.212 mmol) in THF (10 mL) at -100° C. The reaction mixture was stirred for a further 15 minutes at -90° C. and was followed by the addition of acetone (1.675 mL, 22.78 mmol) in THF (10 mL) at -78° C. with stirring over a period of 1 hr. The reaction was monitored by TLC (5% ethylacetate in hexane). The reaction mixture was quenched with aqueous NaHCO3 solution and extracted with ethylacetate. The organic layer was dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (15% ethylacetate in hexane) afforded 200 mg of the product (11% yield).

Workup

  1. stirringThe reaction mixture was stirred for a further 15 minutes at -90° C.
  2. stirringwith stirring over a period of 1 hr
  3. customThe reaction mixture was quenched with aqueous NaHCO3 solution
  4. extractionextracted with ethylacetate
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (15% ethylacetate in hexane)

Sources & evidence

ORD record
ord-b9fe1e24da5b4497b95739457ca2faaa
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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