Ethylene Glycol → HCID 21940732, compound

HRID 1883387Notes

Reaction equation

HRID 1883387 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].I[C:10]1[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=1.[C:17]1([CH2:23][CH2:24][NH2:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=1.C(O)CO.N>O.[Cu]I.C(O)(C)C>[CH3:16][C:12]1[CH:11]=[C:10]([NH:25][CH2:24][CH2:23][C:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=1

Participants

9

Reactant 5

HCID 174Ethylene GlycolHCID 222AmmoniaHCID 122683-IodotolueneHCID 62657Potassium Phosphate, TribasicHCID 769382-(1-Cyclohexenyl)ethylamine

Product 1

HCID 21940732HCID 21940732, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

An oven-dried resealable 15 mL Schlenk tube was charged with CuI (9.6 mg, 0.0504 mmol, 5.0 mol %), K3PO4 (440 mg, 2.07 mmol), evacuated and backfilled with argon. 3-Iodotoluene (130 μL, 1.01 mmol), 2-(1-cyclohexenyl)ethylamine (170 μL, 1.22 mmol), ethylene glycol (115 μL, 1.97 mmol), and isopropyl alcohol (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred magnetically at 80° C. for 22 h. The resulting thick, green-brown suspension was allowed to reach room temperature, poured into a solution of 30% aq ammonia (1 mL) in water (20 mL), and extracted with 3×15 mL of CH2Cl2. The organic phase was dried (Na2SO4), concentrated, and the residue was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 50:1; 15 mL fractions). Fractions 12-17 provided 189 mg (87% yield) of the product as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.06 (t, J=7.4 Hz, 1H), 6.52 (d, J=7.4 Hz, 1H), 6.46−6.39 (m, 2H), 5.53 (m, 1H), 3.57 (br s, 1H), 3.14 (t, J=6.8 Hz, 2H), 2.30−2.22 (m, 5H), 2.07−1.98 (m, 2H), 1.97−1.90 (m, 2H), 1.67−1.52 (m, 4H). 13C NMR (100 MHz, CDCl3): δ 148.5, 138.9, 134.9, 129.1, 123.5, 118.1, 113.6, 109.9, 41.4, 37.6, 27.8, 25.2, 22.8, 22.4, 21.6. IR (neat, cm−1): 3406, 1603, 1590, 1509, 1492, 1478, 1328, 766, 691. Anal. Calcd. for C15H21N: C, 83.67; H, 9.83. Found: C, 83.82; H, 9.84.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  3. customto reach room temperature
  4. extractionextracted with 3×15 mL of CH2Cl2
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated
  7. customthe residue was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 50:1; 15 mL fractions)

Sources & evidence

ORD record
ord-bbd95e28ae1143d0bd51e0983c832943
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

Loading…