Ethylene Glycol → 2-(4-Bromobutyl)-2-methyl-1,3-dioxolane

HRID 2064930

反応式

HRID 2064930 の反応式
N#N.[Br:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:10])[CH3:9].[CH2:11](O)[CH2:12][OH:13].CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CCOCC>[Br:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1([CH3:9])[O:13][CH2:12][CH2:11][O:10]1

参加物

8

反応物 5

HCID 174Ethylene GlycolHCID 947NitrogenHCID 6101p-Toluenesulfonic acidHCID 250616-Bromohexan-2-oneHCID 516892Sodium Bicarbonate

生成物 1

HCID 5600132-(4-Bromobutyl)-2-methyl-1,3-dioxolane

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and a Dean-Stark apparatus under inert atmosphere (N2), a solution of 6-bromo-hexan-2-one (3.34 g, 18.65 mmol) in toluene (71.3 mL) was treated with ethylene glycol (10.4 mL, 186.92 mmol) and TsOH (35 mg, 0.19 mmol). The reaction mixture was heated to reflux for 3 h, allowed to cool to rt and sat. aq. NaHCO3 (100 mL) and ether (100 mL) were added and the aq. phase was washed with water (2×100 mL), dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound. 1H NMR (400 MHz, CDCl3) δ 1.34 (s, 3H), 1.50-1.65 (m, 2H), 1.65-1.75 (m, 2H), 1.84-1.98 (m, 2H), 3.43 (t, J=6.8 Hz, 2H), 3.90-4.04 (m, 4H).

後処理

  1. customIn a flame dried round-bottomed flask equipped with a magnetic stir bar
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 3 h
  4. washthe aq. phase was washed with water (2×100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure

出典と根拠

ORDレコード
ord-844605ff2f0a4743b715a881eff14e13
出典データセット
uspto-grants-2012_10
特許番号
US08288419B2

関連ノート

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