Acetone → HCID 54505728, compound

HRID 345061Notes

Reaction equation

HRID 345061 reaction equation
C([O:4][CH2:5][P:6](=[O:13])([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9])C=C.[CH3:14][C:15]([CH3:17])=[O:16].C[N+]1([O-])CC[O:22]CC1>[Os](=O)(=O)(=O)=O.O>[OH:16][CH:15]([CH2:17][OH:22])[CH2:14][O:4][CH2:5][P:6](=[O:13])([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9]

Participants

6

Reactant 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 11745836HCID 11745836, compound

Product 1

HCID 54505728HCID 54505728, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of diethyl allyloxymethylphosphonate (4.2 g. 20.2 mmol) in an acetone (50 ml) and water (25 ml) mixture, was added osmium tetroxide (1 crystal) and 4-methylmorpholine-N-oxide (3.8 g, 32.3 mmol). The reaction mixture was stirred at 20° C. under nitrogen until no more starting alkene was present (6 days). The solvents were evaporated under high vacuum and the residue chromatographed on silica eluting with chloroform-methanol 10:1 affording diethyl 2,3-dihydroxypropoxymethylphosphonate (4.2 g, 86%) as a clear liquid. νmax (film) 3400, 1650 , 1230, 1100, 1030 and 960 cm-1 ; δH (CDCl3) 1.35(6H, t, J7.3 Hz, 2×CH2CH3), 3.20(2H, s, D2O exchangeable, 2×OH), 3.62(5H, m, CH2OH+CHOH+CH2OCH2P), 3.79(2H, d, 8.2 Hz, CH2P), 4.14(4H, m, 2×CH2CH3); m/z 243 (MH+, 13%); Found: C,38.50; H,7.70%; C8H19O6P.0.4H2O requires C,38.52; H,7.94%.

Workup

  1. custom(6 days)
  2. customThe solvents were evaporated under high vacuum
  3. customthe residue chromatographed on silica eluting with chloroform-methanol 10:1 affording diethyl 2,3-dihydroxypropoxymethylphosphonate (4.2 g, 86%) as a clear liquid

Sources & evidence

ORD record
ord-e903158728cf4af5a25c19aa0253b6ac
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Reaction notes

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