Tetrahydrofuran → Methyl 4-[3-(3-bromophenyl)-1-cyanopropyl]benzoate

HRID 1257450

反応式

HRID 1257450 の反応式
[C:1]([CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)#[N:2].O1CCCC1.C(O[K])(C)(C)C.[Br:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][CH2:33]Br)[CH:27]=1>O.CN(C)C=O>[Br:25][C:26]1[CH:27]=[C:28]([CH2:32][CH2:33][CH:3]([C:4]2[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=2)[C:1]#[N:2])[CH:29]=[CH:30][CH:31]=1

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 848548Methyl 4-(cyanomethyl)benzoateHCID 143612163-Bromophenethyl bromideHCID 178418922HCID 178418922、化合物

生成物 1

HCID 66939300Methyl 4-[3-(3-bromophenyl)-1-cyanopropyl]benzoate収率 55%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a mixed solution of methyl 4-(cyanomethyl)benzoate (3.50 g, 20.0 mmol), tetrahydrofuran (25 mL) and N,N-dimethylformamide (10 ml) was added tert-butoxy potassium (2.69 g, 24.0 mmol) at −78° C., and the mixture was stirred for 30 min. To the reaction mixture was added 1-bromo-3-(2-bromoethyl)benzene (3.37 mL, 22.0 mmol) at the same temperature, and the mixture was stirred under ice-cooling for 4 hr. The reaction mixture was diluted with water, extracted with ethyl acetate, washed successively with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (3.94 g, 55%) as a colorless oil.

後処理

  1. stirringthe mixture was stirred under ice-
  2. temperaturecooling for 4 hr
  3. extractionextracted with ethyl acetate
  4. washwashed successively with water and saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-42dd959c09e7445aa431ff3d0d1e2b41
出典データセット
uspto-grants-2013_06
特許番号
US08461348B2

関連ノート

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