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

HRID 1464525ノート

反応式

HRID 1464525 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-316c513b3521443883167070cb77e4ff
出典データセット
uspto-grants-1994_04
特許番号
US05304658

反応ノート

読み込み中…