Triethyl phosphite → HCID 19027595, compound

HRID 373898Notes

Reaction equation

HRID 373898 reaction equation
[P:1]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])[O:2]CC.[C:11]([O:14][CH2:15][CH:16]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[CH2:17][CH2:18]I)(=[O:13])[CH3:12]>>[C:11]([O:14][CH2:15][CH:16]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[CH2:17][CH2:18][P:1](=[O:2])([O:5][CH2:6][CH3:7])[O:8][CH2:9][CH3:10])(=[O:13])[CH3:12]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 1539121,3-Propanediol, 2-(2-iodoethyl)-, diacetate

Product 1

HCID 19027595HCID 19027595, compound

Procedure

Triethyl phosphite (6.58 g, 6.8 ml, 39.67 mmol) and 4-acetoxy-3-(acetoxymethyl)butyl iodide (5 g, 15.87 mmol) were stirred at 130° C. for 9 hours. The reaction mixture was then allowed to cool and the excess of triethyl phosphite was evaporated under reduced pressure. The product distilled at 235° C./0.3 mm Hg, yield 4.6 g, 75%. 1HNMR: δH (CDCl3) 1.33 (6H, t, J=7Hz, (OCH2CH3)2, 1.74 (5H, m, CHCH2CH2P), 2.06 (6H, s, 2xCOCH3), 4.12 (8H, m, (OCH2CH3)2, 2xCH2OAc). Found: C,47.29; H,7.83%. C13H25O7P 0.25 H2O requires C,47.48; H,7.81%.

Workup

  1. temperatureto cool
  2. customthe excess of triethyl phosphite was evaporated under reduced pressure
  3. distillationThe product distilled at 235° C./0.3 mm Hg, yield 4.6 g, 75%

Sources & evidence

ORD record
ord-8234c96c10b64d60b33a456e0ca19d32
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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