Triethylamine → HCID 17976996, compound

HRID 1588057Notes

Reaction equation

HRID 1588057 reaction equation
Cl[C:2](=[N:11][OH:12])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH2:13]([O:15][P:16]([C:21]([P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])=[CH2:22])(=[O:20])[O:17][CH2:18][CH3:19])[CH3:14].C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[CH2:25]([O:24][P:23]([C:21]1([P:16](=[O:20])([O:15][CH2:13][CH3:14])[O:17][CH2:18][CH3:19])[O:12][N:11]=[C:2]([C:3](=[O:4])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:22]1)(=[O:30])[O:27][CH2:28][CH3:29])[CH3:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 6399041HCID 6399041, compoundHCID 11022954Tetraethyl vinylidene phosphonate

Product 1

HCID 17976996HCID 17976996, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-chloro-2-oximino-1-phenylethanone (I, PREPARATION 8, 0.92 g) and ethenylidene bisphosphonic acid tetraethyl ester (II, PREPARATION 1, 1.50 g) in methylene chloride (5 ml) are treated with triethylamine (1.0 ml) and stirred for 20 hrs. The reaction is diluted with ethyl acetate, washed with water, hydrochloric acid (1N) and saturated sodium bicarbonate, dried with magnesium sulfate and concentrated under reduced pressure. Two reactions of identical size are chromatographed over a silica gel column eluting with ethyl acetate. The appropriate fractions are pooled and concentrated to give the title compound, NMR (CDCl3) 8.11, 8.54, 7.40, 4.23, 3.90 and 1.28 δ.

Workup

  1. washwashed with water, hydrochloric acid (1N) and saturated sodium bicarbonate
  2. dry with materialdried with magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customTwo reactions of identical size are chromatographed over a silica gel column
  5. washeluting with ethyl acetate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d798c216168e49b09fdc67e35025699c
Source dataset
uspto-grants-1993_06
Patent number
US05220021

Reaction notes

Loading…