Dimethylformamide → HCID 10633907, compound

HRID 597555Notes

Reaction equation

HRID 597555 reaction equation
[CH2:1]([OH:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[C-]#N.[Na+].[CH:16](=[CH:23][C:24](=[O:26])[CH3:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O>[O:7]=[C:1]([C:2]1[O:6][CH:5]=[CH:4][CH:3]=1)[CH:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:23][C:24](=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 6228Dimethylformamide3×HCID 7361Furfuryl AlcoholHCID 8929Sodium CyanideHCID 159094-Phenyl-3-Buten-2-one

Product 1

HCID 10633907HCID 10633907, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 38.4 g (0.4 mol) of freshly distilled furfurol and 125 ml of absolute dimethylformamide is added dropwise to a mixture of 9.8 g (0.2 mol) of NaCN and 125 ml of absolute dimethylformamide at 35° C in the course of 45 minutes in a manner analogous to Example 3. Stirring is then continued for 1/2 hour at 35° C. A solution of 43.8 g (0.3 mol) of benzalacetone and 150 ml of absolute dimethylformamide is then added dropwise in the course of 11/2 hours. Stirring is continued at the same temperature for a further 11/2 hours and the reaction mixture is then treated with twice its quantity of water and worked up as described in Example 5. 32.1 g of 1,4-dioxo-1-furyl-2-phenyl-pentane (44% of theoretical) are isolated from 83.5 g of the crude product by distillation; b.p. 147°-148° C/0.4 torr.

Workup

  1. stirringStirring
  2. custom2 hours

Sources & evidence

ORD record
ord-cb8606e11092495485aa9f77c45550d2
Source dataset
uspto-grants-1977_03
Patent number
US04014889

Reaction notes

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