Triethylamine → Methyl 4-[(diethoxyphosphinyl)oxy]-2,6-bis(trifluoromethyl)-3-pyridinecarboxylate
Reaction equation
C(N(CC)CC)C.[P:8]([O-:15])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11].[F:16][C:17]([F:34])([F:33])[C:18]1[C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]([OH:28])[CH:21]=[C:20]([C:29]([F:32])([F:31])[F:30])[N:19]=1>C(Cl)(Cl)(Cl)Cl>[CH2:10]([O:9][P:8]([O:12][CH2:13][CH3:14])([O:28][C:22]1[CH:21]=[C:20]([C:29]([F:32])([F:31])[F:30])[N:19]=[C:18]([C:17]([F:33])([F:16])[F:34])[C:23]=1[C:24]([O:26][CH3:27])=[O:25])=[O:15])[CH3:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Triethylamine (25.2 ml, 0.18 mol) was added dropwise to a cooled (0° C.) solution of diethyl phosphite (23.2 ml, 0.18 mol) and product of Example 4 (50.0 g, 0.17 mol) in carbon tetrachloride (100 ml). The reaction mixture, which had developed a heavy flocculent precipitate, was stirred at 0° C. for 30 minutes before being warmed to room temperature for an additional 24 hours. The reaction mixture was washed consecutively with 1N aq hydrochloric acid (1×250 ml), 0.5N aqueous sodium hydroxide (4×100 ml) and water (1×250 ml) before being dried (MgSO4), filtered and evaporated (aspirator) to a yellow oil (61.53 g). Kugelrohr distillation (120° C. at 25 Pa) afforded the product as a very pale yellow oil (59.03 g). Yield-82%, nD25 1.4197.
Workup
- temperaturebefore being warmed to room temperature for an additional 24 hours
- washThe reaction mixture was washed consecutively with 1N aq hydrochloric acid (1×250 ml), 0.5N aqueous sodium hydroxide (4×100 ml) and water (1×250 ml)
- dry with materialbefore being dried (MgSO4)
- filtrationfiltered
- customevaporated (aspirator) to a yellow oil (61.53 g)
- distillationKugelrohr distillation (120° C. at 25 Pa)
Sources & evidence
- ORD record
- ord-64db6b6c6f2c43699977f89470a61480
- Source dataset
- uspto-grants-1987_04
- Patent number
- US04655816
Reaction notes
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