Bromocyclopentane → Methyl 3-(cyclopentyloxy)-4-methoxy-2-nitrobenzoate

HRID 659053노트

반응식

HRID 659053 반응식
[OH:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].Br[CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:18]1([O:1][C:2]2[C:3]([N+:14]([O-:16])=[O:15])=[C:4]([CH:9]=[CH:10][C:11]=2[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6])[CH2:22][CH2:21][CH2:20][CH2:19]1

참가 물질

5

반응물 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 59268115Methyl 3-hydroxy-4-methoxy-2-nitrobenzoate

생성물 1

HCID 66781723Methyl 3-(cyclopentyloxy)-4-methoxy-2-nitrobenzoate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of methyl 3-hydroxy-4-methoxy-2-nitrobenzoate (1.14 g, 5.0 mmol), bromocyclopentane (0.7 mL, 6.5 mmol), potassium carbonate (2.0 g, 14 mmol), and anhydrous acetonitrile (15 mL) was refluxed under N2. After 19 h, the reaction was allowed to cool to rt, concentrated, and purified by silica gel chromatography (4:1→3:2; hexanes:ethyl acetate) to give methyl 3-(cyclopentyloxy)-4-methoxy-2-nitrobenzoate: MS (ESI): 296.5.

후처리

  1. temperaturewas refluxed under N2
  2. concentrationconcentrated
  3. custompurified by silica gel chromatography (4:1→3:2; hexanes:ethyl acetate)

출처 및 근거

ORD 기록
ord-8201c766f1c3470e9d7ab512b5e95e41
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080563B2

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