Water → 5-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-5-phenylvaleronitrile

HRID 1646821

반응식

HRID 1646821 반응식
I[CH2:2][CH2:3][CH2:4][CH:5]([C:12]1[C:17]([CH3:18])=[C:16]([O:19][CH3:20])[C:15]([CH3:21])=[C:14]([CH3:22])[C:13]=1[O:23][CH3:24])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C-:25]#[N:26].[Na+].C(OC(C)C)(C)C.O>CS(C)=O>[CH3:24][O:23][C:13]1[C:14]([CH3:22])=[C:15]([CH3:21])[C:16]([O:19][CH3:20])=[C:17]([CH3:18])[C:12]=1[CH:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:4][CH2:3][CH2:2][C:25]#[N:26]

참가 물질

6

반응물 4

HCID 962WaterHCID 7914Diisopropyl EtherHCID 8929Sodium CyanideHCID 190880271-Iodo-4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-4-phenylbutane

생성물 1

HCID 190880865-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-5-phenylvaleronitrile수율 163%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
50 °C

실험 절차

To a solution of 4.19 g (5.0 mmole) of 1-iodo-4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-4-phenylbutane in dimethylsulfoxide (30 ml) was added 0.74 g (5×3 mmole) of sodium cyanide, and the mixture was stirred at 50° C. for 2 hours. The reaction solution was cooled with ice, and isopropyl ether and water were added to it, followed by stirring. The isopropyl ether layer was separated out, washed with aqueous sodium chloride solution, dried (magnesium sulfate) and evaporated. The residual solution was chromatographed on a silica gel column to perform purification (elution with isopropyl ether/hexane) to thereby give 1.65 g (98%) of 5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-5-phenylvaleronitrile. Its typical physical properties and nuclear magnetic resonance spectrum data are shown in Table 14.

후처리

  1. additionwere added to it
  2. stirringby stirring
  3. customThe isopropyl ether layer was separated out
  4. washwashed with aqueous sodium chloride solution
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated
  7. customThe residual solution was chromatographed on a silica gel column
  8. custompurification (elution with isopropyl ether/hexane)

출처 및 근거

ORD 기록
ord-073e1732a2dc4675b31c1d894df7e311
출처 데이터셋
uspto-grants-1993_01
특허 번호
US05180742

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