Heptanal → HCID 86671847, compound

HRID 1484404Notes

Reaction equation

HRID 1484404 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH2:9]([O:16][NH2:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[CH2:9]([O:16][N:17]=[CH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 8130HeptanalHCID 102313O-Benzylhydroxylamine

Product 1

HCID 86671847HCID 86671847, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 10 mL round bottom flask equipped with a stifling bar and purged with N2 was added heptanal (343 mg, 420 μL, 3.0 mmol) followed by O-benzylhydroxylamine (369 mg, 349 μL, 3.0 mmol). An immediate evolution of heat occurred with formation of a cloudy solution. The solution was stirred at room temperature during four minutes before 3 mL of dry THF was added. Stirring continued for 20 min, at which time the TLC (hexanes/ethyl acetate, 85:15) indicated completion of reaction. The volatiles were removed under reduced pressure, and the crude material was purified by column chromatography on silica gel using hexanes/ethyl acetate (95:5) as eluent to give 599 mg (91%) of clear oil: Rf=0.48 and 0.51 (two isomers) (hexanes/ethyl acetate, 95:5, v/v); 1H NMR (CDCl3) δ 7.43 (t, 3J=6.3 Hz, 0.6H), 7.36-7.31 (m, 4H), 7.30-7.26 (m, 1H), 6.66 (t, 3J=5.3 Hz, 0.4H), 5.09 (s, 0.8H), 5.04 (s, 1.2H), 2.37-2.33 (m, 0.8H), 2.19-2.15 (m, 1.2H), 1.48-1.42 (m, 2H), 1.34-1.23 (m, 6H), and 0.86 (t, 3J=7.0 Hz, 3H).

Workup

  1. customTo a 10 mL round bottom flask equipped with a stifling bar
  2. custompurged with N2
  3. temperatureAn immediate evolution of heat
  4. additionwas added
  5. customcompletion of reaction
  6. customThe volatiles were removed under reduced pressure
  7. customthe crude material was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-00372125f38249dcb6266845d846c41c
Source dataset
uspto-grants-2016_08
Patent number
US09422233B2

Reaction notes

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