Ethyl Acetate → HCID 593070, compound

HRID 1899779Notes

Reaction equation

HRID 1899779 reaction equation
[H-].[Na+].C(OP([CH2:11][CH:12]=[CH:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(OCC)=O)C.[C:20]([C:22]1[CH:29]=[CH:28][C:25](C=O)=[CH:24][CH:23]=1)#[N:21].C(OCC)(=O)C>O1CCCC1.[Cl-].[Na+].O>[C:20]([C:22]1[CH:29]=[CH:28][C:25]([CH:11]=[CH:12][CH:13]=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:24][CH:23]=1)#[N:21]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 660424-CyanobenzaldehydeHCID 54141095HCID 54141095, compound

Product 1

HCID 593070HCID 593070, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-10 °C

Procedure

The mixture of 60% sodium hydride (7.92 g) in tetrahydrofuran (100 ml) was stirred at -10° C. under nitrogen gas. To reaction mixture was poured ethyl 5-diethoxyphosphoryl-3-pentenoate (49.61 g) and stirred for 1 hour at -10° C. To reaction mixture was poured p-cyanobenzaldehyde (20.00 g) in tetrahydrofuran (50 ml) and stirred for 3 hours at 0° C. The reaction mixture was poured into a mixture of brine and ethyl acetate. The separated organic layer was dried over magnesium sulfate and treated with activated charcoal. After filtration, the filtrate was evaporated in vacuo. The residue was subjected to column chromatography on silica gel and eluted with ethyl acetate/n-hexane=1:4. The fractions containing the object compound were combined and evaporated in vacuo, and give ethyl 5-(4-cyanophenyl)-2,4-pentadienoate (10.04 g).

Workup

  1. customTo reaction mixture
  2. stirringstirred for 1 hour at -10° C
  3. customTo reaction mixture
  4. stirringstirred for 3 hours at 0° C
  5. dry with materialThe separated organic layer was dried over magnesium sulfate
  6. additiontreated with activated charcoal
  7. filtrationAfter filtration
  8. customthe filtrate was evaporated in vacuo
  9. washeluted with ethyl acetate/n-hexane=1:4
  10. additionThe fractions containing the object compound
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-b1729ffb6c194a329d5ee38ffd7f899a
Source dataset
uspto-grants-1996_11
Patent number
US05574016

Reaction notes

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