1-Bromopentane → 3-Methyl-1-pentyloxynaphthalene

HRID 850421

反応式

HRID 850421 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 193632413-Methyl-1-pentyloxynaphthalene収率 12%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-659bfe8676834ed0a5eea9c78d3894c2
出典データセット
uspto-grants-2000_01
特許番号
US06017919

関連ノート

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