Sodium hydride → HCID 15860308, compound

HRID 1291705Notes

Reaction equation

HRID 1291705 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1/[CH:10]=[CH:11]/[C:12]#[N:13].[H-].[Na+].[C:16](CP(=O)(OCC)OCC)#N.F[C:28]1C=CC(OC)=[CH:32][C:29]=1[CH:30]=[O:31]>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C@@H:10]1[CH2:16][C@H:11]1[CH2:12][NH:13][C:30](=[O:31])[CH:29]([CH3:32])[CH3:28]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 27348722-Fluoro-5-methoxybenzaldehydeHCID 70274102HCID 70274102, compound

Product 1

HCID 15860308HCID 15860308, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

(trans)-3-(2-Fluoro-5-methoxyphenyl)-2-propenenitrile: To a suspension of NaH (6.90 g, 60% dispersion in mineral oil, 173 mmol) in THF (500 mL) at 0° C. was added diethyl cyanomethylphosphonate (30.10 g, 170 mmol) dropwise. This was followed by the dropwise addition of a solution of 2-fluoro-5-methoxybenzaldehyde (24.5 g, 159 mmol) in THF (50 mL). The resulting suspension was allowed to warm to ambient temperature. After 18 h, H2O (200 mL) was added and the solution was extracted with EtOAc. The organics were combined, washed with brine, dried over MgSO4, and concentrated to afford a white waxy solid. The material was then purified by Kugelrohr distillation to give the title compound, 24.3 g (86%): mp 56°-57° C.;

Workup

  1. extractionthe solution was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto afford a white waxy solid
  6. distillationThe material was then purified by Kugelrohr distillation

Sources & evidence

ORD record
ord-d0b61c9fe71f453085701ac244dc1921
Source dataset
uspto-grants-1998_05
Patent number
US05753709

Reaction notes

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