Formaldehyde → HCID 178471406, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH:5]([CH2:10][PH:11]([O:13]CC)=O)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2].C(N(C(C)C)CC)(C)C.C[Si]([CH:30]([Si](C)(C)C)[C:31](N)=[O:32])(C)C.[CH2:38]=[O:39]>C1COCC1.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:16])[C:5]([CH2:10][PH:11]([CH2:38][OH:39])=[O:13])([O:32][CH2:31][CH3:30])[CH2:6][CH:7]([CH3:8])[CH3:9])[CH3:2]Participants
Conditions
- Temperature
- 0 °C
Procedure
Crude 2-(ethoxy)phosphinoylmethyl-4-methylpentanoic acid ethyl ester (26 g) was dissolved in 600 mL THF/CH2Cl2 (50/50) and cooled to 0° C. Diisopropyl-ethylamine (32 mL) and 90.8 mL of bis-(trimethylsilyl) acetamide were then added to the solution and the resulting mixture was stirred for 20 minutes before paraformaldehyde (5.5 g) was added. The solution was brought to room temperature and heated at 37° C. for 18 hours. The solvent was removed by evaporation, and the resulting oil dissolved in 200 mL ethyl acetate. The solution was washed with 50 mL of 1N HCl (2×), 50 mL of brine (2×), dried over MgSO4, filtered and evaporated to yield 19.3 g of 2-(ethoxy)(hydroxymethyl)phosphinoylmethyl-4-methylpentanoic acid ethyl ester as a faintly yellow oil, MS: 281 (MH+).
Workup
- additionwas added
- customwas brought to room temperature
- temperatureheated at 37° C. for 18 hours
- customThe solvent was removed by evaporation
- dissolutionthe resulting oil dissolved in 200 mL ethyl acetate
- washThe solution was washed with 50 mL of 1N HCl (2×), 50 mL of brine (2×)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-e106e4a58b8e4ce8b3323d501b663626
- Source dataset
- uspto-grants-2000_01
- Patent number
- US06013792
Reaction notes
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