Sodium Hydroxide → 6-bromo-4,4-dimethyl-8-(propan-2-yl)-3,4-dihydro-2H-chromene

HRID 402783

반응식

HRID 402783 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][C:11]([CH3:13])=[CH2:12])=[C:4]([CH:14]([CH3:16])[CH3:15])[CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+]>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[C:4]([CH:14]([CH3:16])[CH3:15])[CH:3]=1)[O:8][CH2:9][CH2:10][C:11]2([CH3:13])[CH3:12]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 680929374-Bromo-1-[(3-methylbut-3-en-1-yl)oxy]-2-(propan-2-yl)benzene

생성물 1

HCID 452559726-bromo-4,4-dimethyl-8-(propan-2-yl)-3,4-dihydro-2H-chromene

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

4-Bromo-1-[(3-methylbut-3-en-1-yl)oxy]-2-(propan-2-yl)benzene (293 mg, 1.03 mmol) dissolved in dichloromethane (3.10 mL) was cooled to 0° C. and aluminum chloride (138 mg, 1.03 mmol) in dichloromethane (3.0 mL) was added via a syringe. The reaction mixture was stirred at 0° C. for 30 minutes. It was then poured into an Erlenmeyer flask containing a 10% aqueous NaOH solution and ice. The mixture was extracted with dichloromethane (2×), and the combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum. The crude residue was purified by silica gel chromatography, eluting with 0-10% EtOAc/Hexanes to give the title compound as a colorless oil.

후처리

  1. additionIt was then poured into an Erlenmeyer flask
  2. extractionThe mixture was extracted with dichloromethane (2×)
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude residue was purified by silica gel chromatography
  7. washeluting with 0-10% EtOAc/Hexanes

출처 및 근거

ORD 기록
ord-6e14fb9c9c2147cc8acc6489354063c2
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742110B2

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