Diethyl Malonate → HCID 22149831, compound

HRID 703364Notes

Reaction equation

HRID 703364 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5]CC)=O.[F:12][C:13]([F:34])([F:33])[C:14]1[CH:15]=[C:16]([F:32])[C:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([CH:27]=[CH:28][C:29](=[O:31])[CH3:30])=[CH:23][CH:22]=2)=[N:18][CH:19]=1>[Na].C(O)C>[OH:5][C:3]1[CH:2]([C:1]([O:9][CH2:10][CH3:11])=[O:8])[CH:27]([C:24]2[CH:23]=[CH:22][C:21]([O:20][C:17]3[C:16]([F:32])=[CH:15][C:14]([C:13]([F:34])([F:33])[F:12])=[CH:19][N:18]=3)=[CH:26][CH:25]=2)[CH2:28][C:29](=[O:31])[CH:30]=1

Participants

5

Reactant 2

HCID 7761Diethyl MalonateHCID 54562802HCID 54562802, compound

Product 1

HCID 22149831HCID 22149831, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 5360545SodiumSolvent

Procedure

In a 1.0 liter flask was dissolved 2.4 g (0.104 mol) of freshly cut sodium metal in 10 mL of absolute ethanol. To this solution was added a solution of 15.6 g (0.0975 mol) of diethyl malonate in 25 mL of absolute ethanol followed by a solution of 30.2 g (0.0928 mol) of 1-(4-(5-(trifluoromethyl)-3-fluoro-2-pyridyloxy)phenyl)but-1-en-3-one in 75 mL of absolute ethanol. The mixture was stirred at ambient temperature for 6 hours and a cream colored solid precipitated from the solution. The mixture was then diluted with 250 mL of water and the solid slowly dissolved therein. To this solution was slowly added 12 mL of concentrated HCl and the desired product crystallized out of the solution. The product was recovered by filtration, thoroughly washed with water and dried in vacuo. The product melted at 161°-163° C., with decomposition; Rf -0.32 (silica gel, 10:90 MeOH:CHCl3), 1H NMR (CDCl3): δ 1.0 (t, 3H, CH3CH2 --), 2.3-3.1 (m, 2H, ring protons), 3.4-3.75 (m, 2H, ring protons), 3.96 (q, 2H, CH3CH2 --), 5.39 (s, 1H, vinyl), 7.10-8.2 (m, 6H, aromatic), 9.0-11.7 (b, 1H, --OH).

Workup

  1. customprecipitated from the solution
  2. additionThe mixture was then diluted with 250 mL of water
  3. dissolutionthe solid slowly dissolved
  4. customthe desired product crystallized out of the solution
  5. filtrationThe product was recovered by filtration
  6. washthoroughly washed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-c5a8da1d780c42e09c42254e8b86d8e2
Source dataset
uspto-grants-1991_01
Patent number
US04983211

Reaction notes

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