Trolox → HCID 53704167, compound

HRID 2428215Notes

Reaction equation

HRID 2428215 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](O)=[O:15])[CH2:6][CH2:5]2.C(N1C=CN=C1)([N:21]1C=CN=C1)=O>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]([NH2:21])=[O:15])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 40634TroloxHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 53704167HCID 53704167, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (1 equiv.) was dissolved to 0.2 M THF and the stirred pale yellow solution treated with carbonyldiimidazole (CDI) (1.1 equiv.). The reaction was let stir for one hour and a solution of amine (1.1 equiv 0.2 M in THF) was added over one hour and the reaction stirred overnight. The solution was concentrated, dissolved to 0.04 M in CH2Cl2 and washed sequentially with half-volumes of 0.5 M HCl, 1.0 M NaHCO3, saturated NaCl, the organic layer dried over Na2SO4 and concentrated. Flash chromatography yielded the desired 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxamide derivative.

Workup

  1. stirringthe reaction stirred overnight
  2. concentrationThe solution was concentrated
  3. dissolutiondissolved to 0.04 M in CH2Cl2
  4. washwashed sequentially with half-volumes of 0.5 M HCl, 1.0 M NaHCO3, saturated NaCl
  5. dry with materialthe organic layer dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f15142dbe4a54b92a93bdeeb948eec63
Source dataset
uspto-grants-2011_06
Patent number
US07968746B2

Reaction notes

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