Ethyl(3-methoxy-4-nitrobenzyl)methylphosphinate → HCID 178491642, compound

HRID 1948025Notes

Reaction equation

HRID 1948025 reaction equation
C([P:3]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([O:17][CH3:18])[CH:9]=1)(=[O:5])[O-:4])C>Cl>[CH3:18][O:17][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][C:11]=1[N+:14]([O-:16])=[O:15])[CH2:7][CH2:6][PH:3](=[O:4])[OH:5]

Participants

3

Reactant 1

HCID 86654041Ethyl(3-methoxy-4-nitrobenzyl)methylphosphinate2×

Product 1

HCID 178491642HCID 178491642, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of ethyl(3-methoxy-4-nitrobenzyl)methylphosphinate (Compound 216D, 0.500 g, 1.83 mmol) in 37% HCl (5.00 mL) was stirred at 100° C. for 6 hours. The reaction mixture was concentrated under reduced pressure to yield the desired product as a yellow foam, 457.2 mg (102% yield). This material was used in successive reactions without any further purification. 1H NMR (CDCl3, 400 MHz): δ=1.41 (d, J=13.89 Hz, 3H), 3.13 (d, J=16.42 Hz, 2H), 3.97 (s, 3H), 6.89 (d, J=8.08 Hz, 1H), 7.02 (s, 1H), 7.82 (d, J=8.34 Hz, 1H). MS (ES+): m/z 246.05 [MH+] (TOF, polar).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ac3f8dccfb134e079fb7e8ccba9ea982
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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