Potassium Carbonate → HCID 178496529, compound

HRID 511457Notes

Reaction equation

HRID 511457 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[CH2:6][CH2:7][PH:8](=[O:10])[OH:9].Br[CH2:18][CH2:19][O:20][CH3:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[CH2:6][CH2:7][PH:8](=[O:9])[O:10][CH2:18][CH2:19][O:20][CH3:21]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 178491642HCID 178491642, compound2×

Product 1

HCID 178496529HCID 178496529, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (3-methoxy-4-nitrobenzyl)methylphosphinic acid (Compound 216C, 0.250 g, 1.02 mmol) and 1-bromo-2-methoxy ethane (0.287 mL, 3.06 mmol) in DMF (3.0 mL) was charged with potassium carbonate (0.169 g, 1.22 mmol) and n-Bu4NI (0.188 g, 0.510 mmol). The reaction mixture was allowed to heat at 50° C. for 16 hours with stirring. The reaction mixture was quenched with water (10 mL) and extracted with EtOAc (15 mL). The organic layer was washed with water (10 mL), washed with brine (10 mL), dried over Na2SO4, filtered, concentrated under reduced pressure to yield a yellow oil. The crude material was purified by silica gel chromatography on the combi-flash Rf system using 1:1 EtOAc-DCM/MeOH (100:0→90:10) as eluent. The fractions containing product were combined and concentrated under reduced pressure to yield a yellow oil, 0.140 g (45% yield). 1H NMR (CDCl3, 400 MHz): δ=1.47 (d, J=13.89 Hz, 3 H), 3.24 (dd, J=17.43, 3.79 Hz, 2 H), 3.39 (s, 3 H), 3.51-3.62 (m, 2 H), 3.98 (s, 3 H), 4.14 (ddd, J=8.27, 4.42, 4.23 Hz, 2 H), 6.93 (dt, J=8.34, 1.89 Hz, 1 H), 7.12 (t, J=1.77 Hz, 1 H), 7.85 (dd, J=8.21, 0.63 Hz, 1 H). MS (ES+): m/z 304.08 [MH+] (TOF, polar).

Workup

  1. customThe reaction mixture was quenched with water (10 mL)
  2. extractionextracted with EtOAc (15 mL)
  3. washThe organic layer was washed with water (10 mL)
  4. washwashed with brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto yield a yellow oil
  9. customThe crude material was purified by silica gel chromatography on the combi-flash Rf system
  10. additionThe fractions containing product
  11. concentrationconcentrated under reduced pressure
  12. customto yield a yellow oil, 0.140 g (45% yield)

Sources & evidence

ORD record
ord-f66f1914d3ba4742b509ce62fead7cdd
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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