Sodium hydride → methyl (E)-3-(4-cyanophenyl)prop-2-enoate

HRID 726658Notes

Reaction equation

HRID 726658 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)#[N:4].[CH3:13][O:14][C:15]([CH2:17]P(OC)(OC)=O)=[O:16]>O1CCCC1>[C:3]([C:5]1[CH:12]=[CH:11][C:8](/[CH:9]=[CH:17]/[C:15]([O:14][CH3:13])=[O:16])=[CH:7][CH:6]=1)#[N:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 660424-CyanobenzaldehydeHCID 80029Trimethyl phosphonoacetate

Product 1

HCID 11106082methyl (E)-3-(4-cyanophenyl)prop-2-enoateYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring suspension of NaH (6.1 g of 60% oil suspension, 153 mmol) and p-cyanobenzaldehyde (20 g, 153 mmol) in tetrahydrofuran (250 mL) at 0° C. was added via addition funnel a solution of trimethyl phosphonoacetate (28 g, 153 mmol) in tetrahydrofuran (50 mL). After stirring for 48 hours, the solvent was removed in vacuo and the crude residue was dissolved in ethyl acetate (500 mL). The ethyl acetate solution was washed once with water, three times with saturated aqueous NaHSO3 and once with brine. The organic phase was then dried with MgSO4, filtered and concentrated in vacuo to give 28 g (98%) of a white solid.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionthe crude residue was dissolved in ethyl acetate (500 mL)
  3. washThe ethyl acetate solution was washed once with water, three times with saturated aqueous NaHSO3 and once with brine
  4. dry with materialThe organic phase was then dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e2c64c6691349f880e715f75e54514e
Source dataset
uspto-grants-1998_01
Patent number
US05710130

Reaction notes

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