2-Chloro-1,3,2-dioxaphospholane 2-oxide → HCID 86742637, compound

HRID 414768Notes

Reaction equation

HRID 414768 reaction equation
[CH2:1]([O:17][CH2:18][C@H:19]1[C@H:23]([OH:24])[CH2:22][CH2:21][O:20]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Cl[P:26]1(=[O:31])[O:30][CH2:29][CH2:28][O:27]1.[CH:32]([N:35]([CH:38](C)C)[CH2:36]C)(C)C>ClCCCl>[P:26]([O-:27])([O:30][CH2:29][CH2:28][N+:35]([CH3:38])([CH3:36])[CH3:32])([O:24][C@@H:23]1[CH2:22][CH2:21][O:20][C@H:19]1[CH2:18][O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:31]

Participants

5

Reactant 3

HCID 810872-Chloro-1,3,2-dioxaphospholane 2-oxideHCID 81531DiisopropylethylamineHCID 86742639trans-2-Hexadecyloxymethyl-3-hydroxytetrahydrofuran

Product 1

HCID 86742637HCID 86742637, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution containing 1.275 g of dl-trans-2-hexadecyloxymethyl-3-hydroxytetrahydrofuran (prepared as described in Preparation 14), 1.060 g of 2-chloro-2-oxo-1,3,2-dioxaphospholane and 1.30 ml of diisopropylethylamine in 20 ml of 1,2-dichloroethane was heated, with stirring, at 80° C. for 16 hours. The mixture was then cooled, and the solvent was removed by distillation under reduced pressure. The residue was then dissolved in 15 ml of acetonitrile. 3.0 g of trimethylamine gas were passed through and dissolved in the solution, and the resulting reaction mixture was heated in a sealed tube at 80° C. for 18 hours. It was then cooled, and the reaction mixture was evaporated to dryness. The residue was subjected to column chromatography using 50 g of silica gel. The crude substance obtained from the fraction eluted with a 60:35:5 by volume mixture of methylene chloride, methanol and water was further purified by chromatography through two silica gel Lobar B columns. The fraction eluted with the same solvent system as described above gave 1.257 g of the title compound as a white powder, melting at 213°-223° C.

Workup

  1. temperaturewas heated
  2. temperatureThe mixture was then cooled
  3. customthe solvent was removed by distillation under reduced pressure
  4. dissolutionThe residue was then dissolved in 15 ml of acetonitrile
  5. dissolutiondissolved in the solution
  6. customthe resulting reaction mixture
  7. temperaturewas heated in a sealed tube at 80° C. for 18 hours
  8. temperatureIt was then cooled
  9. customthe reaction mixture was evaporated to dryness
  10. customThe crude substance obtained from the fraction
  11. washeluted with a 60:35:5 by volume mixture of methylene chloride, methanol and water
  12. customwas further purified by chromatography through two silica gel Lobar B columns
  13. washThe fraction eluted with the same solvent system

Sources & evidence

ORD record
ord-a474b6ec8a3946cc95c3115d8f87f063
Source dataset
uspto-grants-1988_12
Patent number
US04794183

Reaction notes

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