Allyl iodide → HCID 20085209, compound

HRID 257732Notes

Reaction equation

HRID 257732 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:32](I)[CH:33]=[CH2:34]>C(C(C)=O)C.CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[C:11]([O:13][CH2:34][CH:33]=[CH2:32])=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 15790298HCID 15790298, compound

Product 1

HCID 20085209HCID 20085209, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a 250 mL flask stirring under nitrogen was charged 3.55 g (0.010 mole) of a 4-(4-chlorophenyl)-2-phenyl-2-[(1,2,4-triazol-1-yl)methyl]butanoic acid in 40 mL of methyl ethyl ketone and 10 mL of dimethyl formamide. To the mixture was added 2.07 g (0.015 mole) of potassium carbonate and 1.85 g (0.011 mole) of allyl iodide. The reaction was stirred for 16 hours at 45° C. The reaction was quenched by adding 150 mL of ether and 25 mL of water. The organic phase was washed with 50 mL of saturated sodium bicarbonate and 20 mL of 10% sodium hydroxide, then 50 mL of water. After decolorizing with charcoal, the solvent was filtered and concentrated and gave 2.9 g (79.4% yield) of a solid, Example 137 of Table 1.

Workup

  1. stirringThe reaction was stirred for 16 hours at 45° C
  2. customThe reaction was quenched
  3. additionby adding 150 mL of ether and 25 mL of water
  4. washThe organic phase was washed with 50 mL of saturated sodium bicarbonate and 20 mL of 10% sodium hydroxide
  5. filtrationthe solvent was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1571b0054b19410b9c5fc47a5da09c5e
Source dataset
uspto-grants-1993_11
Patent number
US05264415

Reaction notes

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