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

HRID 659053ノート

反応式

HRID 659053 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-8201c766f1c3470e9d7ab512b5e95e41
出典データセット
uspto-grants-2011_12
特許番号
US08080563B2

反応ノート

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