Triethylamine → HCID 21841052, compound

HRID 1739487Notes

Reaction equation

HRID 1739487 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].C(N(CC)CC)C.[C:18](Cl)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]>C(Cl)Cl>[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 709492,5-Dihydroxybenzaldehyde

Product 1

HCID 21841052HCID 21841052, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-8 °C

Procedure

To a cooled (-8° C.), stirred suspension of 2,5-dihydroxybenzaldehyde (13 g, 93.6 mmol) in of CH2Cl2 (65 ml) (dried over 4A sieves) (65 ml) was added triethylamine (6.5 ml, 46.8 mmol) to give a deep red solution. Pivaloyl chloride (5.6 g, 46.8 mmol) was added portionwise keeping the temperature below 0° C. After the addition was complete the reaction was allowed to warm to ambient temperature and stirred overnight. The reaction was washed with 2N aqueous HCl, water, saturated aqueous NaHCO3 and dried (MgSO4). The organic solution was filtered and evaporated and the residue purified by chromatography (eluant: CH2Cl2 /hexane) to give the title product as a colourless oil which crystallized on standing (4.7 g, 45% based on limiting reagent).

Workup

  1. customto give a deep red solution
  2. customthe temperature below 0° C
  3. additionAfter the addition
  4. temperatureto warm to ambient temperature
  5. stirringstirred overnight
  6. washThe reaction was washed with 2N aqueous HCl, water, saturated aqueous NaHCO3
  7. dry with materialdried (MgSO4)
  8. filtrationThe organic solution was filtered
  9. customevaporated
  10. customthe residue purified by chromatography (eluant: CH2Cl2 /hexane)

Sources & evidence

ORD record
ord-539201b672ac4c2496dcdff52a678502
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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