Dimethylformamide → HCID 22173451, compound

HRID 1646604Notes

Reaction equation

HRID 1646604 reaction equation
C[O-].[Na+].[CH2:4]([C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH2:10][C:11]2=[O:16])[CH:5]=[CH2:6].[CH3:17]N(C)C=O.CI>C(OCC)C>[CH3:17][CH:10]1[CH2:9][C:8]2[C:12](=[CH:13][CH:14]=[CH:15][C:7]=2[CH2:4][CH:5]=[CH2:6])[C:11]1=[O:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 19801174HCID 19801174, compound

Product 1

HCID 22173451HCID 22173451, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent4×

Procedure

1.88 g of sodium methylate in 15 ml of ethyl ether is cooled to 0° C., a solution composed of 2.8 ml of ethyl formiate and 3 g of 4-(2-propenyl)-indanone in 6 ml of ether is introduced over 15 minutes, 5 ml of ether is added, with agitation for 15 minutes, and the suspension is allowed to rise to 20° C. 70 ml of dimethylformamide is added, with agitation for 2 hours, 2.15 ml of methyl iodide and 2 ml of ether are introduced, followed by agitation for 2 hours. The resulting mixture is then poured over 100 ml of ice water and extracted with ethyl ether, the extracts are dried and the solvent is evaporated under reduced pressure. The residue is chromatographed on silica, eluting with a hexane-ethyl acetate mixture (95-5) and 1.62 g of expected product is obtained.

Workup

  1. additionis introduced over 15 minutes
  2. customto rise to 20° C
  3. extractionextracted with ethyl ether
  4. customthe extracts are dried
  5. customthe solvent is evaporated under reduced pressure
  6. customThe residue is chromatographed on silica
  7. washeluting with a hexane-ethyl acetate mixture (95-5)

Sources & evidence

ORD record
ord-16b9943cc6b741f5940f33fc39f54ba8
Source dataset
uspto-grants-1993_01
Patent number
US05180741

Reaction notes

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