Dichloromethane → HCID 53942597, compound

HRID 973616Notes

Reaction equation

HRID 973616 reaction equation
[PH2:1]([OH:3])=[O:2].[CH:4](OCCC)([O:9][CH2:10][CH2:11][CH3:12])[O:5][CH2:6][CH2:7][CH3:8].F[C:18](F)(F)[C:19](O)=O.Cl[CH2:25]Cl>>[CH2:25]([O:2][P:1]([CH:4]([O:5][CH2:6][CH2:7][CH3:8])[O:9][CH2:10][CH2:11][CH3:12])[OH:3])[CH2:18][CH3:19]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 69311Tripropyl orthoformateHCID 4124402Phosphinic Acid

Product 1

HCID 53942597HCID 53942597, compound

Procedure

A mixture of 6.6 g of hypophosphorous acid (95% solution in water) and 86 g of tri-n-propyl orthoformate is treated with 0.77 ml of trifluoracetic acid. The two-phase mixture is stirred at room temperature for 48-72 hours until the reaction is complete. This can be monitored by 31P-NMR or thin layer chromatography. The reaction mixture is diluted with 200 ml of dichloromethane and washed twice with 150 ml of a saturated aqueous solution of sodium bicarbonate. After driving the dichloromethane layer over anhydrous magnesium sulphate and removal of the solvent in vacuo, a colorless oil is obtained which after distillation affords di-n-propyloxymethylphosphonous acid n-propyl ester, b.p. 45°/2×104 mbar.

Workup

  1. washwashed twice with 150 ml of a saturated aqueous solution of sodium bicarbonate
  2. customover anhydrous magnesium sulphate and removal of the solvent in vacuo
  3. customa colorless oil is obtained which
  4. distillationafter distillation

Sources & evidence

ORD record
ord-c411e3e174b3456ab9a6a6900bd7599b
Source dataset
uspto-grants-1991_11
Patent number
US05064819

Reaction notes

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