Chloroacetone → HCID 13215533, compound

HRID 1990914Notes

Reaction equation

HRID 1990914 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7]C)=[O:5])#[N:2].C[O-].[Na+].Cl[CH2:13][C:14](=[O:16])[CH3:15]>CO>[CH3:7][O:6][C:4](=[O:5])[CH:3]([C:1]#[N:2])[CH2:13][C:14](=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 7764Ethyl cyanoacetateHCID 10942334Sodium Methoxide

Product 1

HCID 13215533HCID 13215533, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-cooled (0° C.) solution of ethyl cyanoacetate (6.58 g, 58.1 mmol) in MeOH (20 mL) was slowly added a solution of NaOMe (25% w/v; 58.1 mmol). After 10 min, chloroacetone (5 mL; 62.8 mmol) was slowly added. After 4 h, the solvent was removed. The brown oil was diluted the EtOAc (100 mL) and washed with H2O (100 mL). The organic fraction was dried, filtered, and concentrated to a brown oil (7.79 g; 79%). The oil was a mixture of methyl/ethyl ester products (9/1), and was used without further purification. 1H NMR (200 MHz, CDCl3): δ 1.26 (t, J=7.1 Hz), 2.44 (s, 3H), 3.02 (dd, 1H, J=15.0, 7.0 Hz), 3.42 (dd, 1H, J=15.0, 7.1 Hz), 3.62 (s, 3H), 3.91 (dd, 1H, J=7.2, 7.0 Hz), 4.24 (q, J=7.2 Hz).

Workup

  1. waitAfter 4 h
  2. customthe solvent was removed
  3. additionThe brown oil was diluted the EtOAc (100 mL)
  4. washwashed with H2O (100 mL)
  5. customThe organic fraction was dried
  6. filtrationfiltered
  7. concentrationconcentrated to a brown oil (7.79 g; 79%)
  8. additiona mixture of methyl/ethyl ester products (9/1)
  9. customwas used without further purification

Sources & evidence

ORD record
ord-adfbc98fd35542c8ab43b39a156d42cc
Source dataset
uspto-grants-2010_01
Patent number
US07645754B2

Reaction notes

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