Sodium Iodide → 1-Iodo-4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-4-phenylbutane

HRID 1646820

反応式

HRID 1646820 の反応式
CS(Cl)(=O)=O.[CH3:6][O:7][C:8]1[C:13]([CH3:14])=[C:12]([CH3:15])[C:11]([O:16][CH3:17])=[C:10]([CH3:18])[C:9]=1[CH:19]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:20][CH2:21][CH2:22]O.C(N(CC)CC)C.[I-:37].[Na+]>ClCCl.O>[I:37][CH2:22][CH2:21][CH2:20][CH:19]([C:9]1[C:10]([CH3:18])=[C:11]([O:16][CH3:17])[C:12]([CH3:15])=[C:13]([CH3:14])[C:8]=1[O:7][CH3:6])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 190880534-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-4-phenylbutanol

生成物 1

HCID 190880271-Iodo-4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-4-phenylbutane収率 309.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 1.37 g (10×1.2 mmole) of methanesulfonyl chloride in dichloromethane (10 ml) was added dropwise to 3.28 g (10.0 mmole) of 4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-4-phenylbutan -1-ol and 2.10 ml (10×1.5 mmole) of triethylamine dissolved in dichloromethane (30 ml) at -5° C. over the period of 30 minutes, and the reaction was continued for 20 minutes under stirring, with ice cooling. The reaction was stopped by adding cold water to the reaction solution, and the dichloromethane layer was separated out, washed with cold dilute hydrochloric acid and aqueous sodium chloride solution successively, dried (magnesium sulfate) and evaporated. The residue was dissolved in acetone (50 ml), and 4.5 g (10×3 mmole) of sodium iodide was added to the solution, followed by stirring at 50° C. for 2 hours. The acetone was distilled off, and isopropyl ether and water were added to the residue to extract the product. The isopropyl ether layer was separated out, washed with aqueous sodium chloride solution, and evaporated, and the residual solution was chromatographed on a silica gel column to perform purification (elution with hexane/isopropyl ether) to thereby give 4.07 g (93%) of 1-iodo-4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-4-phenylbutane. Its typical physical properties and nuclear magnetic resonance spectrum data are shown in Table 14.

後処理

  1. customthe dichloromethane layer was separated out
  2. washwashed with cold dilute hydrochloric acid and aqueous sodium chloride solution successively
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated
  5. dissolutionThe residue was dissolved in acetone (50 ml)
  6. stirringby stirring at 50° C. for 2 hours
  7. distillationThe acetone was distilled off
  8. additionisopropyl ether and water were added to the residue
  9. extractionto extract the product
  10. customThe isopropyl ether layer was separated out
  11. washwashed with aqueous sodium chloride solution
  12. customevaporated
  13. customthe residual solution was chromatographed on a silica gel column
  14. custompurification (elution with hexane/isopropyl ether)

出典と根拠

ORDレコード
ord-c569a2daf9ff47639ea12851471d6905
出典データセット
uspto-grants-1993_01
特許番号
US05180742

関連ノート

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