Iodoethane → HCID 178476810, compound

HRID 2279819Notes

Reaction equation

HRID 2279819 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[CH2:6][CH:7]=[CH:8][CH2:9][PH:10](=[O:12])[OH:11].I[CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[CH2:6][CH:7]=[CH:8][CH2:9][PH:10](=[O:11])[O:12][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178490210HCID 178490210, compound2×

Product 1

HCID 178476810HCID 178476810, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (3-methoxy-4-nitrobenzyl)prop-2-en-1-ylphosphinic acid (Compound 37F, 1.28 g, 4.72 mmol) and iodoethane (1.47 g, 9.44 mmol) in DMF (5.0 mL) was charged with potassium carbonate (1.30 g, 9.44 mmol). The reaction mixture was allowed to stir at rt for 16 hours. The reaction mixture was quenched with water (15 mL) and extracted with EtOAc (25 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 on a Teledyne ISCO Combiflash® Rf system using DCM/MeOH (100:0→95:5) as eluent to afford the title compound as 1.08 g of a yellow oil (77%). 1H NMR (CDCl3, 400 MHz): δ=7.84 (d, J=8.3 Hz, 1H), 7.11 (t, J=1.8 Hz, 1H), 6.92 (td, J=1.8, 8.3 Hz, 1H), 5.76-5.90 (m, 1H), 5.18-5.32 (m, 2H), 4.00-4.14 (m, 2H), 3.98 (s, 3H), 3.19 (d, J=16.4 Hz, 2H), 2.60 (dd, J=7.3, 17.7 Hz, 2H), 1.29 (t, J=7.1 Hz, 3H). MS (ESI): m/z 300.10 [M+H]+. UPLC: tR=1.22 min (UPLC-TOF: polar—3 min).

Workup

  1. customThe reaction mixture was quenched with water (15 mL)
  2. extractionextracted with EtOAc (25 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 on a Teledyne ISCO Combiflash® Rf system

Sources & evidence

ORD record
ord-a443cf87aea241179de57b37be55f6fc
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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