Hydrochloric Acid → Ethyl 5-hexadecylamino-2-furancarboxylate

HRID 850971Notes

Reaction equation

HRID 850971 reaction equation
[C:1]([NH:18][C:19]1[O:23][C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:21][CH:20]=1)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].B.Cl>O1CCCC1>[CH2:1]([NH:18][C:19]1[O:23][C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:21][CH:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 20503590HCID 20503590, compound

Product 1

HCID 20503623Ethyl 5-hexadecylamino-2-furancarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.1 g. of ethyl 5-hexadecanamido-2-furancarboxylate and 5 ml. of 1 M borane in tetrahydrofuran is refluxed on the steam bath for 3 hours. After cooling, the reaction is poured into dilute hydrochloric acid and the resulting solid filtered. The solid is dissolved in methylene chloride and the solution is filtered through Magnesol. The solvent is evaporated to yield the product.

Workup

  1. additionA mixture of 1.1 g
  2. temperatureAfter cooling
  3. filtrationthe resulting solid filtered
  4. dissolutionThe solid is dissolved in methylene chloride
  5. filtrationthe solution is filtered through Magnesol
  6. customThe solvent is evaporated
  7. customto yield the product

Sources & evidence

ORD record
ord-248596f9adc14904a19780ceffb3df48
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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