Ethyl cyanoacetate → Ha14-1

HRID 432036Notes

Reaction equation

HRID 432036 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[CH:4][CH:3]=1.[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:12]>C(O)C>[CH3:18][CH2:17][O:16][C:14]([C:13]1[CH:7]([CH:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:11]#[N:12])[C:6]2[CH:9]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[O:10][C:11]=1[NH2:12])=[O:15]

Participants

4

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 728635-Bromosalicylaldehyde2×

Product 1

HCID 3549Ha14-1Yield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of the 5-bromosalicylaldehyde (0.010 mol) in dry ethyl alcohol (30 ml) was added ethyl cyanoacetate (0.022 mol) and 3.0 grams of molecular sieve 3Å powder (Aldrich Chemical Company). The resulting mixture was stirred at room temperature overnight (14 h). Most of the 5-bromosalicylaldehyde disappeared within the first 2 hours as layer chromatography (TLC). The molecular sieve was then filtered off and washed 3 times with tetrahydrofuran. The filtrates were combined and the solvent was removed under vacuum. The residue solidified when incubated at −24° for 2 hours. The desired product was obtained by crystallization in 85% ethanol as a single diastereoisomeric pair. The yield was 86%.

Workup

  1. customdisappeared within the first 2 hours as layer
  2. filtrationThe molecular sieve was then filtered off
  3. washwashed 3 times with tetrahydrofuran
  4. customthe solvent was removed under vacuum
  5. waitincubated at −24° for 2 hours

Sources & evidence

ORD record
ord-c6e141b3e80c49798a80e3c0b1ad1f70
Source dataset
uspto-grants-2003_12
Patent number
US06660871B2

Reaction notes

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