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

HRID 566726노트

반응식

HRID 566726 반응식
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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-8ad9a94d686d46bdb219eae6e7d60c80
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06174901B1

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