Triphenylphosphine → (3-(Ethoxycarbonyl)propyl)triphenylphosphonium Bromide

HRID 1859490Notes

Reaction equation

HRID 1859490 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>C(OCC)C>[Br-:20].[CH2:27]([O:26][C:24]([CH2:23][CH2:22][CH2:21][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:25])[CH3:28]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 2773643(3-(Ethoxycarbonyl)propyl)triphenylphosphonium Bromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of triphenylphosphine (24.6 g; 0.0936 mol) and ethyl 4-bromobutyrate (from Aldrich Chemical Company, Milwaukee, Wis.) (14.4 mL; 0.101 mol) was heated from room temperature to 105° C. over a period of 15-20 minutes, and continued heating the resultant solution at 105° C. for 10 minutes. Allowed the solution to cool, but while still warm cautiously added diethyl ether (50 mL) via a condenser. Triturated the resultant gum to obtain a white powder. Decanted, added fresh diethyl ether (50 mL), and continued trituration for 10 min. Filtered the reaction mixture; washed the filter cake with diethyl ether; and under vacuum removed solvent from the combined filtrate and washings to obtain a mixture of oil and solids. Heated this mixture to 100° C.; cautiously treated with diethyl ether (2×55 mL); and repeated the trituration, filtration, and concentration sequence described above. Combined the two batches of white solids obtained from this process, triturated with toluene (150 mL), filtered, washed the collected solids with toluene and dried under high vacuum to obtain the title salt (11). FABMS 377 (M+) mp 177-179° C.

Workup

  1. temperaturewas heated from room temperature to 105° C. over a period of 15-20 minutes
  2. temperatureAllowed the solution to cool
  3. customTriturated the resultant gum
  4. customto obtain a white powder
  5. customDecanted
  6. additionadded fresh diethyl ether (50 mL)
  7. customfor 10 min
  8. filtrationFiltered the reaction mixture
  9. washwashed the filter cake with diethyl ether
  10. customand under vacuum removed solvent from the combined filtrate and washings
  11. customto obtain
  12. additiona mixture of oil and solids
  13. filtrationthe trituration, filtration, and concentration sequence
  14. customobtained from this process
  15. customtriturated with toluene (150 mL)
  16. filtrationfiltered
  17. washwashed the collected solids with toluene
  18. customdried under high vacuum

Sources & evidence

ORD record
ord-5e9202c3a10a480aaa7eb14412614048
Source dataset
uspto-grants-2003_03
Patent number
US06528522B2

Reaction notes

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