Triethylamine → HCID 86709261, compound

HRID 1050629Notes

Reaction equation

HRID 1050629 reaction equation
[C:1]([O:6][CH2:7][CH2:8]CO)(=[O:5])[C:2]([O-:4])=[O:3].[CH2:11](N(CC)CC)C.ClC(=O)C[P:21](=[O:28])([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24].[C:30]([O:33]CC)(=[O:32])[CH3:31]>>[C:1]([O:6][CH2:7][CH2:8][O:33][C:30]([CH2:31][P:21]([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[O:28])=[O:32])(=[O:5])[C:2]([O:4][CH3:11])=[O:3]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10822542HCID 10822542, compoundHCID 86709262HCID 86709262, compound

Product 1

HCID 86709261HCID 86709261, compoundYield 42%

Procedure

2.0 g (13.51 mmol) of 2-hydroxyethylmethyl oxalate and 1.7 g (16.8 mmol) of triethylamine were dissolved in 50 mL of ethyl acetate, and 3.1 g (14.5 mmol) of diethyl (2-chloro-2-oxoethyl)phosphonate was dropwise added thereto at 15° C. or lower, taking 15 minutes. This was stirred at room temperature for 1 hour, and the disappearance of the starting materials was confirmed through gas chromatography. The reaction liquid was washed with water, the organic layer was concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (ethyl acetate for elution) to give 1.8 g (yield 42%) of the intended 2-(2-(diethoxyphosphoryl)acetoxyl)ethyl methyl oxalate.

Workup

  1. customThe reaction liquid
  2. washwas washed with water
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customthe resulting residue was purified through silica gel column chromatography (ethyl acetate for elution)

Sources & evidence

ORD record
ord-bc11775d59194849bf58191c739ae67b
Source dataset
uspto-grants-2016_07
Patent number
US09384906B2

Reaction notes

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