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

HRID 566726Notes

Reaction equation

HRID 566726 reaction equation
O[C:2]1([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH2:6][C:5](=[O:7])[CH:4]=[C:3]1[C:8]1[CH:9]=[C:10]([CH3:14])[CH:11]=[CH:12][CH:13]=1.OC1(C2C=C(C)C=CC=2)CC(=O)C=C1C1C=CN=CC=1.CN(C1C=CC=CN=1)C.[C:50]([O:53]C(=O)C)(=[O:52])[CH3:51]>C(Cl)Cl>[C:50]([O:53][C:3]1([C:8]2[CH:9]=[C:10]([CH3:14])[CH:11]=[CH:12][CH:13]=2)[CH2:4][C:5](=[O:7])[CH:6]=[C:2]1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)(=[O:52])[CH3:51]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 212664474-Hydroxy-3-pyridine-4-yl-4-m-tolyl-cyclopent-2-en-1-oneHCID 212665484-Hydroxy-4-pyridine-4-yl-3-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-4-pyridine-4-yl-3-m-tolyl-cyclopent-2-en-1-one, and it's regioisomer 4-hydroxy-3-pyridine-4-y1-4-m-toly1-cyclopent-2-en-1-one prepared as described in Example 8, Step E (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 slower 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-8ad9a94d686d46bdb219eae6e7d60c80
Source dataset
uspto-grants-2001_01
Patent number
US06174901B1

Reaction notes

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