Ethyl Acetate → Methyl 2-[5-chloro-2-[4-(4-chloro-5-difluoromethoxy-1-methylpyrazol-3-yl)phenoxymethyl]phenoxy]propanoate

HRID 343284Notes

Reaction equation

HRID 343284 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[N:4][N:5]([CH3:11])[C:6]=1[O:7][CH:8]([F:10])[F:9].[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:33]Cl)=[C:24]([CH:32]=1)[O:25][CH:26]([CH3:31])[C:27]([O:29][CH3:30])=[O:28].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.CCCCCCC>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:33][O:18][C:15]2[CH:16]=[CH:17][C:12]([C:3]3[C:2]([Cl:1])=[C:6]([O:7][CH:8]([F:9])[F:10])[N:5]([CH3:11])[N:4]=3)=[CH:13][CH:14]=2)=[C:24]([CH:32]=1)[O:25][CH:26]([CH3:31])[C:27]([O:29][CH3:30])=[O:28]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 53768369Methyl 2-(2-chloromethyl-5-chlorophenoxy)propionateHCID 1361684484-(4-Chloro-5-difluoromethoxy-1-methylpyrazol-3-yl)phenol

Product 1

HCID 67703354Methyl 2-[5-chloro-2-[4-(4-chloro-5-difluoromethoxy-1-methylpyrazol-3-yl)phenoxymethyl]phenoxy]propanoateYield 45.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8900HeptaneSolvent

Procedure

This compound was prepared in a manner analogous to that of Step I of Example 1, using 0.82 gram (0.0030 mole) of 4-(4-chloro-5-difluoromethoxy-1-methylpyrazol-3-yl)phenol, 0.95 gram (0.0036 mole) of methyl 2-(5-chloro-2-chloromethylphenoxy)propanoate (prepared in Steps A through D of this Example), and 0.62 gram (0.0045 mole) of potassium carbonate in N,N-dimethylformamide. The crude reaction product was subjected to column chromatography on silica gel, using 1:4 ethyl acetate and heptane as the eluant. The product-containing fractions were combined and concentrated under reduced pressure to an oil. The oil was triturated with heptane, yielding 0.68 gram of title compound, mp 61-64° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to that of Step I of Example 1
  2. customThe crude reaction product
  3. concentrationconcentrated under reduced pressure to an oil
  4. customThe oil was triturated with heptane

Sources & evidence

ORD record
ord-dbb49b81868f4a568ef1f1c3012fc1b2
Source dataset
uspto-grants-1999_01
Patent number
US05861359

Reaction notes

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