Iodoethane → Methyl 4-(3-cyanopentan-3-yl)benzoate

HRID 404104

反応式

HRID 404104 の反応式
C[C:2]([CH3:5])([O-])C.[K+].[CH2:7](I)[CH3:8].[C:10]([CH2:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)#[N:11]>C1COCC1>[C:10]([C:12]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)([CH2:2][CH3:5])[CH2:7][CH3:8])#[N:11]

参加物

5

反応物 3

HCID 6340IodoethaneHCID 848548Methyl 4-(cyanomethyl)benzoateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 67150320Methyl 4-(3-cyanopentan-3-yl)benzoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of potassium tert-butoxide (4.81 g) in THF (15 mL) at −30° C. was added a solution of ethyl iodide (4.11 mL) and methyl 4-(cyanomethyl)benzoate (3 g) THF (15 mL) under nitrogen atmosphere over 20 min. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The reaction was quenched by the addition of water (10 mL) and ethyl acetate was added. The organic layer was washed successively with water, brine and dried over anhydrous sodium sulfate. The organic solvent was removed to obtain a residue, which was purified by column chromatography (silicagel, 20% ethyl acetate in petroleum ether) to obtain a crude solid. The crude solid was crystallized using chloroform in petroleum ether to afford the title compound.

後処理

  1. customThe reaction was quenched by the addition of water (10 mL) and ethyl acetate
  2. additionwas added
  3. washThe organic layer was washed successively with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe organic solvent was removed
  6. customto obtain a residue, which
  7. customwas purified by column chromatography (silicagel, 20% ethyl acetate in petroleum ether)
  8. customto obtain a crude solid
  9. customThe crude solid was crystallized

出典と根拠

ORDレコード
ord-f1efd629e5534efeae474dc7bd1d1da7
出典データセット
uspto-grants-2014_06
特許番号
US08748426B2

関連ノート

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