Water → Ethyl 5-methyl-4-(2-propenyloxy)-2,6-bis(trifluoromethyl)-3-pyridinecarboxylate

HRID 542132Notes

Reaction equation

[F:1][C:2]([F:21])([F:20])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([OH:14])[C:6]([CH3:15])=[C:5]([C:16]([F:19])([F:18])[F:17])[N:4]=1.C([O-])([O-])=O.[K+].[K+].[CH2:28](Br)[CH:29]=[CH2:30].O>CN(C=O)C>[CH3:15][C:6]1[C:7]([O:14][CH2:30][CH:29]=[CH2:28])=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:3]([C:2]([F:20])([F:1])[F:21])=[N:4][C:5]=1[C:16]([F:19])([F:18])[F:17]

Participants

Conditions

Temperature: 25 °C

Procedure

To a mixture of 10 g (0.03 mol) of product of Example 35 with 9.7 g (0.07 mol) of K2CO3 in 100 ml of DMF was charged 8 g (0.07 mol) of allyl bromide. The resulting mixture was stirred at 25° C. for 4 days. The reaction mixture was poured into H2O, and extracted with duethyl ether. The ether phase was dried (MgSO4), and concentrated in vacuo to 10.2 g (95%) of product as a yellow oil: nD25 1.4334

Workup

extractionextracted with duethyl ether
dry with materialThe ether phase was dried (MgSO4)
concentrationconcentrated in vacuo to 10.2 g (95%) of product as a yellow oil

Sources & evidence

ORD record: ord-9bd21468539540f8a0d4250ea6a92c05
Source dataset: uspto-grants-1987_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04655816

Reaction notes

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