Tetrahydrofuran → HCID 14836222, compound

HRID 1087760Notes

Reaction equation

HRID 1087760 reaction equation
[CH2:1]([CH:12]1[NH:16][C:15](=[O:17])[NH:14][C:13]1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C1COCC1.COCCO[AlH2-]OCCOC.[Na+]>C1(C)C=CC=CC=1>[CH2:1]([CH:12]1[CH2:13][NH:14][C:15](=[O:17])[NH:16]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14836221HCID 14836221, compoundHCID 16684438Red-Al

Product 1

HCID 14836222HCID 14836222, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A dry 250 ml round bottom flask equipped with a nitrogen inlet, reflux condenser and stirring bar was charged with 2.44 g of 5-undecylhydantoin and 100 ml of THF. To this was added dropwise 10 ml of 3.5M Vitride in toluene. After the initial foaming had ceased the reaction mixture was refluxed for 30 hours. The reaction was quenched with saturated sodium sulfate solution and extracted with 3×50 ml of ether. The combined ether extracts were dried, filtered and concentrated. Recrystallization from ether gave 1.8 g (78%) of white crystals, m.p. 97°-99° C.

Workup

  1. customA dry 250 ml round bottom flask equipped with a nitrogen inlet
  2. temperaturereflux condenser
  3. temperaturewas refluxed for 30 hours
  4. customThe reaction was quenched with saturated sodium sulfate solution
  5. extractionextracted with 3×50 ml of ether
  6. dry with materialThe combined ether extracts were dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customRecrystallization from ether

Sources & evidence

ORD record
ord-127403408f9647488995308e959a8df0
Source dataset
uspto-grants-1990_10
Patent number
US04960771

Reaction notes

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