4-Nitrobenzoic Acid → Methyl [6-(4-nitrobenzoyl)-2H-1,3-benzodioxol-5-yl]acetate

HRID 442662노트

반응식

HRID 442662 반응식
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=2[O:2]1.[N+:15]([C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=1)([O-:17])=[O:16].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C([O-])([O-])=O.[K+].[K+]>C(Cl)CCl.O>[CH2:1]1[O:2][C:3]2[C:8](=[CH:7][C:6]([C:22](=[O:23])[C:21]3[CH:20]=[CH:19][C:18]([N+:15]([O-:17])=[O:16])=[CH:26][CH:25]=3)=[C:5]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:4]=2)[O:9]1

참가 물질

7

반응물 4

HCID 61084-Nitrobenzoic AcidHCID 11430Potassium CarbonateHCID 14812Phosphorus oxide (P4O10)HCID 266588Methyl 2-(1,3-dioxaindan-5-yl)acetate

생성물 1

HCID 404213Methyl [6-(4-nitrobenzoyl)-2H-1,3-benzodioxol-5-yl]acetate수율 50%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 962Water용매

실험 절차

To a solution of methyl 3,4-methylenedioxyphenylacetate (5.4 g, 28 mmol) in ClCH2CH2Cl (100 mL) was added 4-nitrobenzoic acid (7.2 g, 43 mmol) and P2O5 (18 g) at room temperature under argon. The mixture was refluxed for 28 h, cooled to room temperature, then cold water was added slowly. The resulting mixture was carefully neutralized with solid K2CO3, and extracted with 1:1 hexane/EtOAc (2×300 mL). The combined extracts were washed with water and brine, and dried over Na2SO4. The solvent was removed in vacuo and the resulting residue was separated by chromatography (3:1 hexane/EtOAc) to afford the title compound as a yellow solid (4.7 g, 14 mmol, 50%). 1H NMR (CDCl3) 8.32 (d, 2H, J=8.5), 7.92 (d, 2H, J=8.5), 6.85 (s, 1H), 6.81 (s, 1H), 6.07 (s, 2H), 3.88 (s, 2H), 3.63 (s, 3H).

후처리

  1. temperatureThe mixture was refluxed for 28 h
  2. extractionextracted with 1:1 hexane/EtOAc (2×300 mL)
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe resulting residue was separated by chromatography (3:1 hexane/EtOAc)

출처 및 근거

ORD 기록
ord-e7efa73de63944e1bb9d22e90b559737
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05891871

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