Ethanolamine → HCID 67262915, compound

HRID 1755564Notes

Reaction equation

HRID 1755564 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([OH:16])=O)[CH2:6][CH2:5]2.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:31]([CH2:33][NH2:34])[OH:32]>C1COCC1>[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([NH:34][CH2:33][CH2:31][OH:32])=[O:16])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 700EthanolamineHCID 40634TroloxHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 67262915HCID 67262915, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (5.00 g 19.98 mmol) in 150 mL THF was treated with 3.65 g CDI (22.5 mmol) and the exothermic reaction let stir for 1 h at room temperature. Ethanolamine (1.35 g, 22.10 mmol) in 50 mL THF was added over 1 h and the solution stirred overnight. The reaction was concentrated, dissolved into 375 mL CH2Cl2 and washed with 250 mL 0.1 M HCl, 250 mL 0.5 M NaHCO3, 2×100 mL saturated NaCl and dried over Na2SO4. The acidic aqueous phase was extracted 3×100 mL CH2Cl2 and washed with 50 mL saturated NaCl and dried over Na2SO4. The combined organics were concentrated and purified by flash chromatography yielding 2.88 g of 6-hydroxy-N-(2-hydroxyethyl)-2,5,7,8-tetramethylchroman-2-carboxamide as an off white impure solid.

Workup

  1. customthe exothermic reaction
  2. stirringthe solution stirred overnight
  3. concentrationThe reaction was concentrated
  4. dissolutiondissolved into 375 mL CH2Cl2
  5. washwashed with 250 mL 0.1 M HCl, 250 mL 0.5 M NaHCO3, 2×100 mL saturated NaCl
  6. dry with materialdried over Na2SO4
  7. extractionThe acidic aqueous phase was extracted 3×100 mL CH2Cl2
  8. washwashed with 50 mL saturated NaCl
  9. dry with materialdried over Na2SO4
  10. concentrationThe combined organics were concentrated
  11. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c574bf142bf245fd86dbf49a05495e82
Source dataset
uspto-grants-2015_10
Patent number
US09169196B2

Reaction notes

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