1-Bromopentane → 3-Methyl-1-pentyloxynaphthalene

HRID 850421

반응식

HRID 850421 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH2:20][CH2:21][CH2:22][CH3:23]>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([O:12][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

참가 물질

5

반응물 3

HCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 261351-Naphthol, 3-methyl-

생성물 1

HCID 193632413-Methyl-1-pentyloxynaphthalene수율 12%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

The crude product of 3-methylnaphthalen-1-ol, dimethylformamide (DMF, 20 ml), potassium carbonate (3 g, 21.7 mmol) and pentyl bromide (4.0 ml, 32.3 mmol) were mixed in a reaction vessel replaced with argon, and this solution was stirred at 90° C. for 3 hours. DMF was evaporated under reduced pressure, and water (20 ml) was added. The aqueous layer was extracted with ethyl acetate (20 ml) 3 times. The organic layer was washed with saturated brine (20 m1l) and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (hexane/ethyl acetate=100/0-50/1) to give 3-methyl-1-pentyloxynaphthalene (827 mg, 12% in 3 steps) as a colorless oil.

후처리

  1. customDMF was evaporated under reduced pressure, and water (20 ml)
  2. additionwas added
  3. extractionThe aqueous layer was extracted with ethyl acetate (20 ml) 3 times
  4. washThe organic layer was washed with saturated brine (20 m1l)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe drying agent was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by column chromatography (hexane/ethyl acetate=100/0-50/1)

출처 및 근거

ORD 기록
ord-659bfe8676834ed0a5eea9c78d3894c2
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06017919

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