HCID 178476798, compound → HCID 178491642, compound

HRID 511458Notes

Reaction equation

HRID 511458 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[CH2:6][CH2:7][PH:8](=[O:12])[O:9]CC>Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[CH2:6][CH2:7][PH:8](=[O:9])[OH:12]

Participants

3

Reactant 1

HCID 178476798HCID 178476798, compound2×

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, 3 H), 3.13 (d, J=16.42 Hz, 2 H), 3.97 (s, 3 H), 6.89 (d, J=8.08 Hz, 1 H), 7.02 (s, 1 H), 7.82 (d, J=8.34 Hz, 1 H). MS (ES+): m/z 246.05 [MH+] (TOF, polar).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c35d0060b5ca466d84b14b16812985ed
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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