Formaldehyde → Diisopropyl hydroxymethylphosphonate

HRID 2105261Notes

Reaction equation

HRID 2105261 reaction equation
[CH2:1]=[O:2].C(N(CC)CC)C.[CH:10]([O:13][PH:14](=[O:19])[O:15][CH:16]([CH3:18])[CH3:17])([CH3:12])[CH3:11]>>[OH:2][CH2:1][P:14](=[O:19])([O:15][CH:16]([CH3:18])[CH3:17])[O:13][CH:10]([CH3:12])[CH3:11]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 3072Diisopropyl phosphiteHCID 8471Triethylamine

Product 1

HCID 10867235Diisopropyl hydroxymethylphosphonateYield 86.9%

Procedure

To a suspension of paraformaldehyde (3.4 g) in diisopropylphosponate (25 g) was added triethylamine (2 mL). The reactants were heated in a 130° oil bath with vigorous stirring for 4 h. The volatiles were removed on a rotavap and the residue was chromatographed on silica gel using ethyl acetate to afford 19.3 g of material. 1H NMR(DMSO-d6) δ 1.23 (d, 12H), 3.62 (dd, 2H), 4.59 (m, 2H), 5.31 (m, 1H)

Workup

  1. temperatureThe reactants were heated in a 130° oil bath
  2. customThe volatiles were removed on a rotavap
  3. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-d8cadb760330430fbbda29843ac5b2eb
Source dataset
uspto-grants-2009_08
Patent number
US07579332B2

Reaction notes

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