Acetic Acid → 1-Ethyl-4-(3,4,5-trimethoxyphenyl)-1-(2-thienyl)butyl isocyanide

HRID 1708965Notes

Reaction equation

HRID 1708965 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([N+:9]#[C-:10])[CH2:7][CH3:8].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH2:23][CH2:24][CH2:25]Cl)[CH:16]=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20].C(O)(=O)C.C(OCC)(=O)C>O1CCCC1.O>[CH2:7]([C:6]([N+:9]#[C-:10])([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[CH2:25][CH2:24][CH2:23][C:15]1[CH:16]=[C:17]([O:21][CH3:22])[C:18]([O:19][CH3:20])=[C:13]([O:12][CH3:11])[CH:14]=1)[CH3:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 3151993-(3,4,5-Trimethoxyphenyl)propyl chlorideHCID 152885881-(2-Thienyl)propyl isocyanide

Product 1

HCID 108323281-Ethyl-4-(3,4,5-trimethoxyphenyl)-1-(2-thienyl)butyl isocyanideYield 71.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2 g of diisopropylamine in 10 ml of tetrahydrofuran is cooled at -60° C and 10 ml of 1.6 M n-butyl lithium in hexane are added dropwise to the solution. The mixture is stirred at the same temperature for 30 minutes to give a solution of lithium diisopropylamide. A solution of 2 g of 1-(2-thienyl)propyl isocyanide in 10 ml of tetrahydrofuran is added dropwise at -60° C. to the solution obtained above and the mixture is stirred at the same temperature for 30 minutes. A solution of 3.8 g of 3-(3,4,5-trimethoxyphenyl)propyl chloride in 5 ml of tetrahydrofuran is added dropwise to the mixture at the same temperature, and said mixture is stirred for 1 hour. The reaction mixture is neutralized with acetic acid, and ethyl acetate and water are added thereto. The organic layer is separated therefrom, washed with an aqueous saturated sodium chloride solution, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=4:1) to give 3.4 g of 1-ethyl-4-(3,4,5-trimethoxyphenyl)-1-(2-thienyl)butyl isocyanide as a colorless oil. yield: 71.5%

Workup

  1. customobtained above and the mixture
  2. stirringis stirred for 1 hour
  3. additionare added
  4. customThe organic layer is separated
  5. washwashed with an aqueous saturated sodium chloride solution
  6. customdried
  7. customevaporated
  8. customto remove solvent
  9. customThe residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-1c93b6324fa340b2ab92202ad82fea2b
Source dataset
uspto-grants-1990_08
Patent number
US04946862

Reaction notes

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