tert-Butanol → 4,6-Di-tert-butyl-5-hydroxy-2-methylbenzofuran

HRID 1900514ノート

反応式

HRID 1900514 の反応式
CS(O)(=O)=O.[C:6]([C:10]1[C:15]2[CH:16]=[C:17]([CH3:19])[O:18][C:14]=2[CH:13]=[CH:12][C:11]=1[OH:20])([CH3:9])([CH3:8])[CH3:7].[C:21](O)([CH3:24])([CH3:23])[CH3:22].[OH-].[Na+]>C(Cl)(Cl)Cl>[C:6]([C:10]1[C:15]2[CH:16]=[C:17]([CH3:19])[O:18][C:14]=2[CH:13]=[C:12]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:11]=1[OH:20])([CH3:9])([CH3:8])[CH3:7]

参加物

6

反応物 4

HCID 6386tert-ButanolHCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 234428664-t-Butyl-5-hydroxy-2-methylbenzofuran

生成物 1

HCID 184331674,6-Di-tert-butyl-5-hydroxy-2-methylbenzofuran収率 11.2%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

Methanesulfonic acid (1.2 ml) was added dropwise to a chloroform solution of 4-tert-butyl-5-hydroxy-2-methylbenzofuran (250 mg, 1.2 mmol) and tert-butyl alcohol (500 mg, 6.0 mmol) under cooling with ice. After stirring at 0° C. for 15 min, the mixture was poured into ice water. The mixture was then neutralized with 1N aqueous sodium hydroxide and subjected to extraction with ethyl acetate. The extracted layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (n-hexane) to afford 4,6-di-tert-butyl-5-hydroxy-2-methylbenzofuran (35 mg) as a pale yellow oil. Mass 260(M+), 245, 57

後処理

  1. temperatureunder cooling with ice
  2. extractionsubjected to extraction with ethyl acetate
  3. washThe extracted layer was washed with a saturated aqueous solution of sodium hydrogen carbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel chromatography (n-hexane)

出典と根拠

ORDレコード
ord-d18e2f867ac44d57930fe873784ee504
出典データセット
uspto-grants-1996_11
特許番号
US05574178

反応ノート

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