Sodium hydride → tert-Butyl (4-tert-butyl-3-methoxyphenoxy)acetate

HRID 1350819

反応式

HRID 1350819 の反応式
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[O:14][CH3:15])([CH3:6])([CH3:5])[CH3:4].Br[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>O1CCCC1>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:9][C:8]=1[O:14][CH3:15])([CH3:6])([CH3:4])[CH3:5]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 122529764-Tert-butyl-3-methoxyphenol

生成物 1

HCID 58640411tert-Butyl (4-tert-butyl-3-methoxyphenoxy)acetate収率 79.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

To a suspension of 60% sodium hydride (96 mg, 2.4 mmol) in tetrahydrofuran (THF) (10 ml) was added 4-tert-butyl-3-methoxyphenol (360 mg, 2 mmol) at 0° C., followed by additional stirring for 30 minutes. Then, tert-butyl bromoacetate (468 mg, 2.4 mmol) was added and the mixture was refluxed at 80° C. for 1 hour. The reaction was then quenched with saturated aqueous solution of ammonium chloride and the crude product was extracted with ethylacetate. The organic layer was separated, washed with brine, dried over magnesium sulfate. Then, filtration, evaporation to remove the solvent under reduced pressure gave the residue, which was applied to a silica gel chromatography column and eluted with a volume mixture of hexane and ethylacetate (20/1 to 4/1) to furnish 466 mg (79% yield) of the title compound as a white solid.

後処理

  1. customThe reaction was then quenched with saturated aqueous solution of ammonium chloride
  2. extractionthe crude product was extracted with ethylacetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationThen, filtration, evaporation
  7. customto remove the solvent under reduced pressure
  8. customgave the residue, which
  9. washeluted with a volume mixture of hexane and ethylacetate (20/1 to 4/1)

出典と根拠

ORDレコード
ord-b7e96e3207f6426ca9545b444befa29f
出典データセット
uspto-grants-2007_05
特許番号
US07214824B2

関連ノート

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