Ethylene Glycol → HCID 21940676, compound

HRID 1883386Notes

Reaction equation

HRID 1883386 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[NH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15].C(O)CO.I[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1.N>C(O)CCC.O.[Cu]I>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])=[CH:22][CH:23]=1

Participants

9

Reactant 5

HCID 174Ethylene GlycolHCID 222AmmoniaHCID 62657Potassium Phosphate, TribasicHCID 696764-IodoanisoleHCID 756345-Aminopentan-1-ol

Product 1

HCID 21940676HCID 21940676, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 2631-ButanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

An oven-dried resealable 15 mL Schlenk tube was charged with CuI (9.5 mg, 0.0499 mmol, 5.0 mol %), K3PO4 (440 mg, 2.07 mmol), evacuated and backfilled with argon. 5-Amino-1-pentanol (135 μL, 1.24 mmol), ethylene glycol (0.11 mL, 1.97 mmol), and a solution of 4-iodoanisole (235 mg, 1.00 mmol) in 1-butanol (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred magnetically at 100° C. for 14 h. The resulting thick, yellow-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; ethyl acetate; 15 mL fractions). Fractions 6-15 provided 177 mg (85% yield) of the product as a pale tan oil. 1H NMR (400 MHz, CDCl3): δ 6.80−6.74 (m, 2H), 6.60−6.54 (m, 2H), 3.74 (s, 3H), 3.65 (t, J=6.4 Hz, 2H), 3.07 (t, J=7.0 Hz, 2H), 2.5 (br s, 2H), 1.68−1.55 (m, 4H), 1.52−1.41 (m, 2H). 13C NMR (100 MHz, CDCl3): δ 151.9, 142.6, 114.8, 114.0, 62.7, 55.8, 44.9, 32.4, 29.4, 23.3. IR (neat, cm−1): 3350, 1511, 1233, 1036, 820. Anal. Calcd. for C12H19NO2: C, 68.87; H, 9.15. Found: C, 68.93; H, 9.12.

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; ethyl acetate; 15 mL fractions)

Sources & evidence

ORD record
ord-67718cc5691e4b9faaee5f6e1d907091
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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