Diethyl vinylphosphonate → HCID 19801586, compound

HRID 1646174Notes

Reaction equation

HRID 1646174 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1.[CH:15]([P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])=[CH2:16]>CN(C)C=O.C(N(CC)CC)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:19]([O:18][P:17]([O:21][CH2:22][CH3:23])(/[CH:15]=[CH:16]/[C:2]1[CH:3]=[C:4]([NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1)=[O:24])[CH3:20]

Participants

6

Reactant 2

HCID 69629Diethyl vinylphosphonateHCID 302657Ethyl 2-((3-bromophenyl)amino)acetate

Product 1

HCID 19801586HCID 19801586, compoundYield 60.5%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
95 °C

Procedure

A solution of ethyl N-(3-bromophenyl)glycinate (Example B) (4 g, 15.5 mmol), diethyl vinylphosphonate (4.92 g, 30 mmol), and bis(triphenylphosphine) palladium (II) chloride (1 g) in dimethylformamide (15 ml) and triethyamine (5 ml) is immersed in an oil bath (95° C.) and stirred for 20 hours. After cooling the dimethylformamide is removed in vacuo and the oily brown residue is dissolved in a saturated solution of sodium chloride and extracted with chloroform. The chloroform layer is dried over magnesium sulfate, filtered and evaporated to give a residue (3.2 g). Purification is accomplished by silica gel chromatography (ethyl acetate as eluant, a single fluorescent spot on tlc, Rf=0.5 (ethyl acetate)).

Workup

  1. customis removed in vacuo
  2. dissolutionthe oily brown residue is dissolved in a saturated solution of sodium chloride
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-46158ea397104952ba56d989571bf4a3
Source dataset
uspto-grants-1993_01
Patent number
US05179085

Reaction notes

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