Sodium hydride → HCID 54348092, compound

HRID 1377753Notes

Reaction equation

HRID 1377753 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH:14]1([O:19][C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=2[O:28][CH3:29])[CH:23]=O)[CH2:18][CH2:17][CH2:16][CH2:15]1>C1COCC1.CCOCC>[CH:14]1([O:19][C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=2[O:28][CH3:29])[CH:23]=[CH:5][C:3]#[N:4])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehyde

Product 1

HCID 54348092HCID 54348092, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a slurry of NaH (1.1 g, 27.5 mmol) in 80 mL of THF at 0° C. was added dropwise a solution of diethyl cyanomethylphosphonate (4.42 g, 24.9 mmol) in 20 mL of THF. The mixture was stirred for 30 min, and a solution of 3-cyclopentoxy-4-methoxybenzaldehyde (5.0 g, 22.7 mmol) in 20 mL of THF was then added dropwise. The mixture was for 2 hr and then diluted with ether. The mixture was washed with 1M H3PO4, H2O, and brine. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to yield 3-cyclopentoxy-4-methoxycinnamonitrile (4.8 g, 87%) as a yellow oil, which was carried on without further purification. 1H-NMR (300 MHz): δ 3.89 (s, 3), 5.69 (d, 1, J=16.6).

Workup

  1. waitThe mixture was for 2 hr
  2. washThe mixture was washed with 1M H3PO4, H2O, and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-00604dc297b146fda5313abdf2e93087
Source dataset
uspto-grants-1997_09
Patent number
US05665754

Reaction notes

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