Potassium Carbonate → HCID 13132209, compound

HRID 325595Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12](=[O:23])[CH:13]([O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:31]1[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][N:32]=1>CS(C)=O>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12](=[O:23])[CH:13]([O:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][N:32]=2)=[CH:20][CH:21]=1)[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

31.6 g of 2-benzyloxyethyl-2-(4-hydroxyphenoxy)propionate were dissolved in 100 ml of dimethylsulfoxide, 15.2 g of potassium carbonate were added thereto, then the mixture was heated at 90° C. for one hour with stirring. 20.0 g of 2-chloro-5-trifluoromethylpyridine were added dropwise to this solution which was then maintained at 90° C. for a further two hours. After cooling the reaction solution to room temperature, it was poured into ice-water, then extracted with ether. The ether layer was dried and filtered, and the ether was distillated off. The end product of 2-benzyloxyethyl-2-[4-(5-trifluoromethyl-2-pyridyloxy)-phenoxy]propionate (a compound also produced in Example 20) was obtained in a yield of 41.0 g (m.p. 44°-47° C.).

Workup

temperaturewas then maintained at 90° C. for a further two hours
temperatureAfter cooling the reaction solution to room temperature
extractionextracted with ether
dry with materialThe ether layer was dried
filtrationfiltered

Sources & evidence

ORD record: ord-3e36a1a819274c60a6e8c7e8783b1a81
Source dataset: uspto-grants-1984_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04441913

Reaction notes

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