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

HRID 1257450

반응식

HRID 1257450 반응식
[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

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 848548Methyl 4-(cyanomethyl)benzoateHCID 143612163-Bromophenethyl bromideHCID 178418922HCID 178418922, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-42dd959c09e7445aa431ff3d0d1e2b41
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461348B2

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