Triethyl phosphite → tert-Butyl diethylphosphonoacetate

HRID 593470Notes

Reaction equation

HRID 593470 reaction equation
[P:1]([O:8]CC)([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].Br[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>>[C:16]([O:15][C:13](=[O:14])[CH2:12][P:1]([O:2][CH2:3][CH3:4])([O:5][CH2:6][CH3:7])=[O:8])([CH3:19])([CH3:18])[CH3:17]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 79177tert-Butyl bromoacetate

Product 1

HCID 2773685tert-Butyl diethylphosphonoacetateYield 97%

Conditions

Temperature
90 °C

Procedure

Triethyl phosphite (485 g) is warmed up to 90° C. under N2 atmosphere in a three-necked round-bottomed flask, and t-butyl bromoacetate (541 g) is added dropwise into the system within 2 h. Then the mixture is kept stirring at 90° C. for around 4 h, and then cooled to room temperature. The obtained mixture is distilled under vacuo to remove compounds with low boiling point, and the residue is collected as a colorless liquid compound 5 in 97% yield (680 g) and >98% GC purity.

Workup

  1. temperaturecooled to room temperature
  2. distillationThe obtained mixture is distilled under vacuo
  3. customto remove compounds with low boiling point
  4. customthe residue is collected as a colorless liquid compound 5 in 97% yield (680 g) and >98% GC purity

Sources & evidence

ORD record
ord-cb79ee36c6cc4462ba09a415da06dd43
Source dataset
uspto-grants-2016_01
Patent number
US09242965B2

Reaction notes

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