Hydrochloric Acid → 4,6-Di-t-butyl-5-hydroxy-2-methyl-2-(4-nitrophenoxymethyl)-2,3-dihydrobenzofuran

HRID 367313ノート

反応式

HRID 367313 の反応式
C([O:4][C:5]1[C:6]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:7][C:8]2[O:12][C:11]([CH3:24])([CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)[CH2:10][C:9]=2[C:25]=1[C:26]([CH3:29])([CH3:28])[CH3:27])(=O)C.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].Cl>C1(C)C=CC=CC=1>[C:26]([C:25]1[C:9]2[CH2:10][C:11]([CH3:24])([CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)[O:12][C:8]=2[CH:7]=[C:6]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:5]=1[OH:4])([CH3:29])([CH3:28])[CH3:27]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 232880295-Acetoxy-4,6-di-t-butyl-2-methyl-2-(4-nitrophenoxymethyl)-2,3-dihydrobenzofuran

生成物 1

HCID 154857314,6-Di-t-butyl-5-hydroxy-2-methyl-2-(4-nitrophenoxymethyl)-2,3-dihydrobenzofuran収率 36.4%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Under a nitrogen atmosphere, 1.0 g of 5-acetoxy-4,6-di-t-butyl-2-methyl-2-(4-nitrophenoxymethyl)-2,3-dihydrobenzofuran was dissolved in 30 ml of toluene. To the solution was added 5.5 ml of diisobutyl aluminum hydride (1.0 M in toluene) and the mixture was stirred at room temperature for 2 hours. After reaction, the reaction solution was combined with a saturated aqueous ammonium chloride solution and 10% hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The concentrate was purified by silica gel column chromatography eluting with n-hexane containing 5% ethyl acetate to give 0.33 g of 4,6-di-t-butyl-5-hydroxy-2-methyl-2-(4-nitrophenoxymethyl)-2,3-dihydrobenzofuran as a pale yellow oil (yield 36%).

後処理

  1. customAfter reaction
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography
  7. washeluting with n-hexane containing 5% ethyl acetate

出典と根拠

ORDレコード
ord-ad47c02c47bf4a97a08ae8b0dd76c968
出典データセット
uspto-grants-2000_10
特許番号
US06133279

反応ノート

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