Iodomethyl pivalate → 2-[5-(3,5-Dichlorophenylthio)-4-isopropyl-2-methyl-imidazol-1-ylmethoxy]ethyl-2,2-dimethylpropionyloxymethyl ether

HRID 1005543Notes

Reaction equation

HRID 1005543 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][O:16][CH2:17][CH2:18][OH:19])[C:13]([CH3:20])=[N:12][C:11]=2[CH:21]([CH3:23])[CH3:22])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:24]([O:30][CH2:31]I)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26]>>[CH3:26][C:25]([CH3:28])([CH3:27])[C:24]([O:30][CH2:31][O:19][CH2:18][CH2:17][O:16][CH2:15][N:14]1[C:10]([S:9][C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=2)=[C:11]([CH:21]([CH3:23])[CH3:22])[N:12]=[C:13]1[CH3:20])=[O:29]

Participants

3

Reactant 2

HCID 104401Iodomethyl pivalateHCID 4781812-[5-(3,5-Dichloro-phenylsulfanyl)-4-isopropyl-2-methyl-imidazol-1-ylmethoxy]-ethanol

Product 1

HCID 4781872-[5-(3,5-Dichlorophenylthio)-4-isopropyl-2-methyl-imidazol-1-ylmethoxy]ethyl-2,2-dimethylpropionyloxymethyl etherYield 32.3%

Procedure

The compound 8 (375 mg, 1 mmol) was alkylated with the pivaloyloxymethyl iodide (1.21 g, 5 mmol) under potassium carbonate (415 mg, 3 mmol) in the same manner as the example 61 to give the compound 77 (158 mg, 32%) as oil. Rf 0.26 (1:1 EtOAc - hexane).

Sources & evidence

ORD record
ord-6a7c0406897748ad92cebe9d6a1de0c0
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Reaction notes

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