Octanal → HCID 86671848, compound

HRID 1484405Notes

Reaction equation

HRID 1484405 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[O-]S([O-])(=O)=O.[Na+].[Na+].[CH2:17]([O:24][NH2:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N#N>ClCCl>[CH2:17]([O:24][N:25]=[CH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 454OctanalHCID 947NitrogenHCID 24436Sodium SulfateHCID 102313O-Benzylhydroxylamine

Product 1

HCID 86671848HCID 86671848, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Octanal (385 mg, 469 μL, 3.0 mmol) was weighed into a 10 mL round bottom flask previously flushed with N2 and containing a stifling bar. To the flask was anhydrous Na2SO4 (4.26 g, 30 mmol), 6 mL of dry dichloromethane and finally, O-benzylhydroxylamine (369 mg, 349 μL, 3 mmol) over 2 min while maintaining positive N2 pressure. The reaction mixture was stirred overnight. The salt was filtered off and rinsed with dichloromethane. The combined filtrates and rinsings were concentrated. The crude material was purified by column chromatography on silica gel eluting with hexanes/ethyl acetate (95:5) to give 328 mg (47%) of a clear oil: Rf=0.45 and 0.51 (two isomers) (hexanes/ethyl acetate, 95:5, v/v); 1H NMR (CDCl3) δ 7.43 (t, 3J=6.3 Hz, 0.5H), 7.36-7.25 (m, 5H), 6.66 (t, 3J=5.5 Hz, 0.5H), 5.08 (s, 1H), 5.03 (s, 1H), 2.37-2.32 (m, 1H), 2.18-2.14 (m, 1H), 1.49-1.41 (m, 2H), 1.33-1.18 (m, 8H), and 0.86 (t, 3J=7 Hz, 3H). Exact mass (FAB+) calculated for C15H24NO [M+H] 234.1852. Found 234.1856.

Workup

  1. custompreviously flushed with N2
  2. additioncontaining a stifling bar
  3. filtrationThe salt was filtered off
  4. washrinsed with dichloromethane
  5. concentrationThe combined filtrates and rinsings were concentrated
  6. customThe crude material was purified by column chromatography on silica gel eluting with hexanes/ethyl acetate (95:5)

Sources & evidence

ORD record
ord-b6261aa4711c40dcbcd6aa46216b1bf3
Source dataset
uspto-grants-2016_08
Patent number
US09422233B2

Reaction notes

Loading…