HCID 86641268, compound → HCID 14475773, compound

HRID 386354Notes

Reaction equation

HRID 386354 reaction equation
[C:1]([O:5][CH2:6][CH2:7][CH2:8][P:9](=[O:20])([O:15][Si](C)(C)C)[O:10][Si](C)(C)C)(=[O:4])[CH:2]=[CH2:3]>CO>[C:1]([O:5][CH2:6][CH2:7][CH2:8][P:9](=[O:10])([OH:20])[OH:15])(=[O:4])[CH:2]=[CH2:3]

Participants

3

Reactant 1

HCID 86641268HCID 86641268, compound

Product 1

HCID 14475773HCID 14475773, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Di(trimethylsilyl) 3-acryloyloxypropylphosphonate (40 g; 0.118 moles) is dissolved in MeOH (130 ml). The solution is stirred at room temperature for 2 hours. The solvent is vacuum distilled on a rotary evaporator to afford the product as a highly viscous, colorless oil, which solidified after a few days upon storage (22.7 g; yield 99%). 1H NMR (DMSO-d6, δ ppm) 1.78-2.00 (m, 4H, CH2—CH2—P), 4.20 (t, 2H, CH2—O), 4.91 (s, 2H, (HO)2—P), 5.94 (dd, 1H, CH═), 6.16 (dd, 1H, CH═), 6.39 (dd, 1H, CH═). 31P NMR (DMSO-d6, δ ppm) 31.71.

Workup

  1. distillationdistilled on a rotary evaporator
  2. customto afford the product as a highly viscous, colorless oil, which
  3. waitsolidified after a few days upon storage (22.7 g; yield 99%)

Sources & evidence

ORD record
ord-b233da87fe4841f4943235f8a47d839c
Source dataset
uspto-grants-2013_02
Patent number
US08372516B2

Reaction notes

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