Nitrogen → HCID 43090068, compound

HRID 531390Notes

Reaction equation

HRID 531390 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].C(=O)([O-])[O-].[K+].[K+].N#N.Br[CH2:20][CH2:21][CH2:22][OH:23]>C1OCCOCCOCCOCCOCCOC1.CC(C)=O>[OH:23][CH2:22][CH2:21][CH2:20][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanol

Product 1

HCID 43090068HCID 43090068, compoundYield 105.1%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 180AcetoneSolvent

Procedure

4-hydroxyacetophenone (10.0 g, 73.5 mmol), 18-crown-6 (0.2912 g, 1.1 mmol) and potassium carbonate (13.2 g, 95.5 mmol) were taken in a two neck round bottom flask equipped with a stir bar. The flask was vacuumed and refilled with N2 three times. Acetone (22 mL) was added through syringe and needle. The mixture was stirred at room temperature for 30 minutes, followed by addition of 1-bromo-3-propanol (7.8 mL, 88.1 mmol). The mixture was refluxed for 24 hours and then filtered. Acetone was removed under vacuum to yield the crude product (15.0 g) which was used in the next step without purification. Purification can be performed by column chromatography (30% ethyl acetate and 70% hexane): mp 37-41° C.; 1H NMR (500 MHz, DMSO-d6) δ 1.86-1.91 (m, 2H), 2.50 (s, 3H, overlap with DMSO), 3.56 (m, 2H), 4.13 (t, J=6.36 Hz, 2H), 4.55 (t, J=5.14 Hz, 1H), 7.03 (d, J=8.80 Hz, 2H), 7.92 (d, J=9.05 Hz, 2H); 13C NMR (125 MHz, DMSO-d6) δ 26.3 (s), 31.9 (s), 57.1 (s), 64.9(s), 114.1(s), 129.7 (s), 130.3 (d), 162.5 (s), 196.1 (s); IR (ATR) ν 3439, 2941, 1654, 1595, 1255, 1170, 1056, 948, 827 cm-1; MS (ESI) m/z calc for C11H14NaO3 [MNa]+ 217.1, found 216.8. NMR results were consistent with the previously reported characterization in CDCl3.4

Workup

  1. customequipped with a stir bar
  2. temperatureThe mixture was refluxed for 24 hours
  3. filtrationfiltered
  4. customAcetone was removed under vacuum

Sources & evidence

ORD record
ord-1d963457465441838dc4def427afc080
Source dataset
uspto-grants-2016_05
Patent number
US09353214B2

Reaction notes

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