Isopropanol → Dipropan-2-yl(4-nitrophenyl)phosphonate

HRID 511222Notes

Reaction equation

HRID 511222 reaction equation
[CH3:1][CH:2]([OH:4])[CH3:3].[CH2:5](N(CC)CC)C.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([P:21](Cl)(Cl)=[O:22])=[CH:17][CH:16]=1)([O-:14])=[O:13].CCO[C:28]([CH3:30])=[O:29]>>[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([P:21](=[O:22])([O:29][CH:28]([CH3:30])[CH3:5])[O:4][CH:2]([CH3:3])[CH3:1])=[CH:17][CH:16]=1)([O-:14])=[O:13]

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 13486298(4-Nitrophenyl)phosphonic dichloride

Product 1

HCID 11572803Dipropan-2-yl(4-nitrophenyl)phosphonateYield 25%

Procedure

A solution of distilled dry propan-2-ol (20 ml) and triethylamine (1.0 g, 10 mmol) was added dropwise to (4-nitrophenyl)phosphonic dichloride (1.2 g, 5 mmol) at 0° C. The resulting mixture was stirred at reflux overnight, the mixture filtered and the filtrate concentrated under reduced pressure to yield a crude product, which was purified by chromatography over silica gel eluting with petroleum ether:EtOAc: 5:1 to afford 360 mg of desired dipropan-2-yl (4-nitrophenyl)phosphonate (yield: 25%). 1H-NMR (CDCl3, 400 MHz): δ=1.18 (d, J=6.0 Hz, 6 H), 1.33 (d, J=6.4 Hz, 6 H), 4.65-4.73 (m, 2 H), 7.93 (dd, J=8.8, 12.8 Hz, 2 H), 8.22 (dd, J=3.2, 8.8 Hz, 2 H).

Workup

  1. temperatureat reflux overnight
  2. filtrationthe mixture filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customto yield a crude product, which
  5. customwas purified by chromatography over silica gel eluting with petroleum ether

Sources & evidence

ORD record
ord-d09f6be7053345c586193bc1e745b82a
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

Loading…