Diethyl vinylphosphonate → HCID 85850734, compound

HRID 1454341Notes

Reaction equation

HRID 1454341 reaction equation
[CH:1]([P:3](=[O:10])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6])=[CH2:2].CO[CH2:13][N:14]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:15][Si](C)(C)C>C(Cl)Cl>[CH2:20]([N:14]1[CH2:13][CH2:2][CH:1]([P:3](=[O:10])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6])[CH2:15]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 69629Diethyl vinylphosphonateHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine

Product 1

HCID 85850734HCID 85850734, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6.0 g (36.6 mmol) of diethyl vinylphosphonate and 11 mL (44 mmol) of N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine in 150 mL of CH2Cl2 at 0° C. was stirred for 30 min. The reaction mixture was washed with 150 mL of 1N NaHCO3 and 150 mL of sat'd NaCl. The organic layer was dried over Na2SO4 and concentrated. The residue was purified on a 40L Biotage column using 3:2 and 1:1 v/v hexane/acetone as the gradient to afford 9.44 g (87%) of the title compound as a pale yellow oil: RF: 0.24 (3:2 v/v hexane/acetone); 1H-NMR (500 MHz) δ 1.32 (t, J=7.0, 6H), 2.04-2.12 (m, 2H), 2.39-2.58 (m, 3H), 2.83 (m, 1H), 2.97 (m, 1H), 3.64 (s, 2H), 4.06-4.16 (m, 4H), 7.24-7.34 (m, 5H); ESI-MS 298 (M+H); LC-1: 1.2 min.

Workup

  1. washThe reaction mixture was washed with 150 mL of 1N NaHCO3 and 150 mL of sat'd NaCl
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified on a 40L Biotage column

Sources & evidence

ORD record
ord-b4028c206726409c8ab3283c2bc2588e
Source dataset
uspto-grants-2009_01
Patent number
US07479504B2

Reaction notes

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