Sodium hydride → (E)-1-iodo-3-[2-(4-methoxyphenyl)ethenyl]benzene

HRID 1297535Notes

Reaction equation

HRID 1297535 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[CH2:7]P(=O)(OCC)OCC.[CH:19](=O)[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1.[NH4+].[Cl-]>C1COCC1>[I:3][C:4]1[CH:18]=[CH:17][CH:16]=[C:6](/[CH:7]=[CH:19]/[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 312444-MethoxybenzaldehydeHCID 58999960Diethyl 3-iodobenzylphosphonate

Product 1

HCID 11013106(E)-1-iodo-3-[2-(4-methoxyphenyl)ethenyl]benzeneYield 93.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of NaH (2 mmol, 80% suspension in oil), and 3-iodobenzylphosphonate 13 (450 mg, 1.27 mmol) in 7 mL of THF at 80° C. under nitrogen atmosphere, was added dropwise p-anisaldehyde (172 mg, 1.27 mmol). After 3 days at room temperature, NH4Cl solution (saturated, 5 mL) was added and the mixture was extracted with CH2Cl2 (3×30 mL). The combined organic extract was dried over Na2SO4, evaporated and purified by flash chromatography (EtOAc: Hex, 1:9) to give (E)-1-iodo-3-[2-(4-methoxyphenyl)ethenyl] benzene 8 (400 mg, 90%). 1H NMR (200 MHz, CDCl3): δ 3.84 (s, 3H), 6.84 (d, J=16.29 Hz, 1H), 6.90 (m, 2H), 7.05 (d, J=16.30 Hz, 1H), 7.07 (t, J=7.8 Hz, 1H), 7.42–7.56 (m, 4H), 7.85 (s, 1H); 13C NMR (50 MHz, CDCl3): δ 55.32, 94.76, 114.20, 124.85, 125.48, 127.88, 129.58, 129.62, 130.25, 135.00, 135.91, 139.97, 159.62; HRMS: m/z Calcd for C15H13IO: 336.0011; Found: 336.0006.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (3×30 mL)
  2. extractionThe combined organic extract
  3. dry with materialwas dried over Na2SO4
  4. customevaporated
  5. custompurified by flash chromatography (EtOAc: Hex, 1:9)

Sources & evidence

ORD record
ord-80025e2cfecd4628b734f01b2d219626
Source dataset
uspto-grants-2007_07
Patent number
US07250525B2

Reaction notes

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