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

HRID 367313노트

반응식

HRID 367313 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-ad47c02c47bf4a97a08ae8b0dd76c968
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06133279

반응 노트

불러오는 중…