Diethanolamine → HCID 20703758, compound

HRID 2428280Notes

Reaction equation

HRID 2428280 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.[NH:31]([CH2:35][CH2:36][OH:37])[CH2:32][CH2:33][OH:34]>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]([N:31]([CH2:35][CH2:36][OH:37])[CH2:32][CH2:33][OH:34])=[O:16])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 8113DiethanolamineHCID 40634TroloxHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 20703758HCID 20703758, compoundYield 9.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (500 mg, 2.00 mmol) in 10 mL THF was added 356 mg CDI (2.20 mmol). After stirring for 1.5 h., a solution of diethanolamine (231 mg, 2.2 mmol) in 10 mL THF was added over 1 h and the reaction was stirred overnight. The reaction was concentrated, dissolved into 70 mL CH2Cl2 and washed sequentially with 50 mL 0.62 M HCl, 50 mL 1.0 M NaHCO3, 50 mL saturated NaCl and dried over Na2SO4. The combined aqueous phases were extracted 3×50 mL 3:1 isopropyl alcohol/isopropyl acetate which was dried and concentrated to a brown oil. Flash chromatography yielded 63 mg of 6-hydroxy-N,N-bis(2-hydroxyethyl)-2,5,7,8-tetramethylchroman-2-carboxamide as a yellow oil.

Workup

  1. stirringthe reaction was stirred overnight
  2. concentrationThe reaction was concentrated
  3. dissolutiondissolved into 70 mL CH2Cl2
  4. washwashed sequentially with 50 mL 0.62 M HCl, 50 mL 1.0 M NaHCO3, 50 mL saturated NaCl
  5. dry with materialdried over Na2SO4
  6. extractionThe combined aqueous phases were extracted 3×50 mL 3:1 isopropyl alcohol/isopropyl acetate which
  7. customwas dried
  8. concentrationconcentrated to a brown oil

Sources & evidence

ORD record
ord-9ac4534efe644af1b37105b28995a04f
Source dataset
uspto-grants-2011_06
Patent number
US07968746B2

Reaction notes

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