Trimethyl phosphite → HCID 86709731, compound
Reaction equation
[CH3:1][O:2][CH:3]([O:12][CH3:13])[CH2:4][N:5]=[CH:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1.Cl[C:15]([O:17][CH2:18][CH3:19])=[O:16].[P:20]([O:25]C)([O:23][CH3:24])[O:21][CH3:22]>C1COCC1>[CH3:22][O:21][P:20]([CH:6]([N:5]([CH2:4][CH:3]([O:2][CH3:1])[O:12][CH3:13])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)(=[O:25])[O:23][CH3:24]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
To the oil obtained in Step i (16.3 g, 82.3 mmol) was added 60 mL THF under a N2 atmosphere. The reaction was cooled to −10° C. (MeOH/ice) and fitted with an internal thermometer. Ethyl chloroformate (7.9 mL, 82.3 mmol) was added dropwise keeping the internal temperature at or below −9.5° C. The reaction was stirred for 10 minutes at −10° C. and then the bath was removed and the reaction was allowed to warm to room temperature. Using an ice bath as a heat sink, trimethyl phosphite (10.7 mL, 90.5 mmol) was added. The reaction was allowed to gradually warm to room temperature and was stirred overnight. The solvent was removed on a rotary evaporator. Toluene was added and evaporated on a rotary evaporator. The toluene addition and evaporation was then carried out a second time.
Workup
- customfitted with an internal thermometer
- custombelow −9.5° C
- customthe bath was removed
- temperatureto warm to room temperature
- additionwas added
- temperatureto gradually warm to room temperature
- stirringwas stirred overnight
- customThe solvent was removed on a rotary evaporator
- additionToluene was added
- customevaporated on a rotary evaporator
- additionThe toluene addition and evaporation
Sources & evidence
- ORD record
- ord-adeea295b86f47f5ad49ac17ec584b17
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09260450B2
Reaction notes
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