Hydrochloric Acid → 3,4-Bis(4-methoxyphenyl)hex-3-ene

HRID 28273

反応式

HRID 28273 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][CH3:11])=[CH:5][CH:4]=1.Cl>O1CCCC1>[CH3:6][CH2:9]/[C:10](/[C:11]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)=[C:9](\[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)/[CH2:11][CH3:10]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 671444-Propanoylanisole

生成物 1

HCID 30325393,4-Bis(4-methoxyphenyl)hex-3-ene収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A slurry of titanium trichloride (1.54 gm, 10.0 mmol) in 30 ml dry tetrahydrofuran was prepared under an inert atmosphere, and powdered lithium aluminum hydride (190 mg, 5.0 mmol) was cautiously added. The resulting solution was stirred for two hours at room temperature to form the Ti(II) reagent, and a solution of para-methoxypropiophenone (820 mg, 5 mmol) in 5 ml dry tetrahydrofuran was added. The reaction was refluxed for four hours, and then poured into 50 ml 2 N aqueous hydrochloric acid. The solution was extracted several times with ether, and the ether extracts were combined, washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated by solvent removal at the rotary evaporator. The residue was purified by chromatography on alumina to give 630 mg (85% yield) dimestrol; mp 124°.

後処理

  1. temperatureThe reaction was refluxed for four hours
  2. extractionThe solution was extracted several times with ether
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated by solvent removal at the rotary evaporator
  6. customThe residue was purified by chromatography on alumina

出典と根拠

ORDレコード
ord-a464d353bb1d4f3289accc4fbd7d44d8
出典データセット
uspto-grants-1980_09
特許番号
US04225734

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