Methyl cyanoacetate → HCID 3100846, compound

HRID 1586630Notes

Reaction equation

HRID 1586630 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([CH2:21][C:22]([O:24][CH3:25])=[O:23])#[N:20]>N1CCCCC1>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[C:21]([C:19]#[N:20])[C:22]([O:24][CH3:25])=[O:23])=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7747Methyl cyanoacetateHCID 755064-(Benzyloxy)-3-methoxybenzaldehyde

Product 1

HCID 3100846HCID 3100846, compound

Reagents, catalysts & solvents 1

HCID 8082PiperidineCatalyst

Procedure

A mixture of 4-(benzyloxy)-3-methoxybenzaldehyde (1.21 g, 0.005 mol), methyl cyanoacetate (0.50 g, 0.005 mol) methanol (10.0 mL) and piperidine (5 drops) is heated and stirred at reflux for 1 hour and cooled. The product, 3-(4-benzyloxy-3-methoxyphenyl)-2-cyano-2-propenoate is collected by filtration, washed with methanol and dried in air. The yield is 1.50 g (93%) of product having an absorption maximum at 364 nm in methylene chloride solution. The identity of the product is supported by mass spectrometry.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hour
  3. temperaturecooled
  4. filtrationThe product, 3-(4-benzyloxy-3-methoxyphenyl)-2-cyano-2-propenoate is collected by filtration
  5. washwashed with methanol
  6. customdried in air

Sources & evidence

ORD record
ord-27da911ea4a54fb78691528ee11c473d
Source dataset
uspto-grants-1993_06
Patent number
US05215876

Reaction notes

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