Dimethylformamide → 2-Bromo-5-[(cyclobutyloxy)methyl]-1,3-dimethoxybenzene

HRID 41244ノート

反応式

HRID 41244 の反応式
[CH:1]1([OH:5])[CH2:4][CH2:3][CH2:2]1.CN(C=O)C.[H-].[Na+].[Br:13][C:14]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([CH2:22]Cl)=[CH:16][C:15]=1[O:24][CH3:25]>CCCCCCC.C(OCC)(=O)C.C(OCC)(=O)C.O>[Br:13][C:14]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([CH2:22][O:5][CH:1]2[CH2:4][CH2:3][CH2:2]2)=[CH:16][C:15]=1[O:24][CH3:25]

参加物

8

反応物 4

HCID 6228Dimethylformamide2 回HCID 24758Sodium hydrideHCID 76218CyclobutanolHCID 249719722-Bromo-5-(chloromethyl)-1,3-dimethoxybenzene

生成物 1

HCID 579124482-Bromo-5-[(cyclobutyloxy)methyl]-1,3-dimethoxybenzene収率 85.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 21899848Ethylacetate heptane溶媒

実験手順

To a mixture of cyclobutyl alcohol (4.16 g, 57.7 mmol) and DMF (30 mL) was added sodium hydride (60% oil dispersion: 2.31 g, 57.7 mmol) while cooling on ice, and the mixture was stirred at room temperature for one hour. To the mixture was gradually added dropwise a mixture of 2-bromo-5-(chloromethyl)-1,3-dimethoxybenzene (2.47 g, 9.3 mmol) and DMF (30 mL), and the mixture was stirred at room temperature for one hour. Water was added to the mixture while cooling on ice, and then ethyl acetate was added. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=4/1) to obtain the title compound (2.39 g, 7.94 mmol).

後処理

  1. temperaturewhile cooling on ice
  2. additionTo the mixture was gradually added dropwise
  3. stirringthe mixture was stirred at room temperature for one hour
  4. temperaturewhile cooling on ice
  5. stirringAfter thoroughly shaking the mixture
  6. customthe organic layer was separated
  7. washthe organic layer was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationThe mixture was filtered
  10. distillationthe solvent in the filtrate was distilled off under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

出典と根拠

ORDレコード
ord-5b659e429b134b459463fc5cd1122af5
出典データセット
uspto-grants-2013_09
特許番号
US08530504B2

反応ノート

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