Acetic Anhydride → 4-Acetoxy-3-pyridine-4-yl-4-m-tolyl-cyclopent-2-en-1-one

HRID 566720Notes

Reaction equation

HRID 566720 reaction equation
[OH:1][C:2]1([C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)[CH2:6][C:5](=[O:7])[CH:4]=[C:3]1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.CN(C1C=CC=CN=1)C.[C:30](OC(=O)C)(=[O:32])[CH3:31]>C(Cl)Cl>[C:30]([O:1][C:2]1([C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)[CH2:6][C:5](=[O:7])[CH:4]=[C:3]1[C:8]1[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=1)(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 212664474-Hydroxy-3-pyridine-4-yl-4-m-tolyl-cyclopent-2-en-1-one

Product 1

HCID 212665564-Acetoxy-3-pyridine-4-yl-4-m-tolyl-cyclopent-2-en-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxy-3-pyridine-4-yl-4-m-tolyl-cyclopent-2-en-1-one and it's regioisomer (265 mg, 1.0 mmole) in methylene chloride (5 mL) was added dimethylamino pyridine (183 mg, 1.5 mmole) and acetic anhydride (0.12 mL, 1.2 mmole) at r.t. The reaction mixture was stirred at that temperature for 1 hr before quenching the reaction with 1 mL of methanol. Concentration and purification (silica, hexane/ethyl acetate) gave the title compound as the faster eluting isomer. MS (m/z): Calcd. C19H17NO3(M+): 307, found (M+H)+: 308.1.

Workup

  1. custombefore quenching
  2. customthe reaction with 1 mL of methanol
  3. concentrationConcentration and purification (silica, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4529830da61142c5ad931844f6e16d99
Source dataset
uspto-grants-2001_01
Patent number
US06174901B1

Reaction notes

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