Water → HCID 86743487, compound

HRID 2352574Notes

Reaction equation

HRID 2352574 reaction equation
C([Li])CCC.[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)C=CC=CC=1.[CH:34]([C@H:36]1[N:40]([CH3:41])[C:39](=[O:42])[CH2:38][C@H:37]1[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=O.O>C1(C)C=CC=CC=1>[CH3:41][N:40]1[C@H:36]([CH:34]=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)[C@H:37]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:38][C:39]1=[O:42]

Participants

6

Reactant 4

HCID 962WaterHCID 13825986HCID 13825986, compoundHCID 16731599[(3-Chlorophenyl)methyl](triphenyl)phosphanium bromideHCID 178418339Butyllithium

Product 1

HCID 86743487HCID 86743487, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

32.8 g (77 mmol) of n-butyllithium (15% in hexane) were added dropwise under nitrogen with ice cooling to 36.0 g (77 mmol) of triphenyl-m-chlorobenzylphosphonium bromide in 150 ml of toluene in the course of 20 minutes, and the orange suspension was subsequently stirred for 15 minutes. 15.6 g (77 mmol) of cis-5-formyl-1-methyl-4- phenylpyrrolidin-2-one (German Laid-Open Application DOS 3,537,075 and 3,632,589; J. Org. Chem. 52 (1987), 4352) in 120 ml of toluene were then added dropwise and stirred in at room temperature for 3 hours (color change toward pale yellow). 200 ml of H2O were then added, the mixture was acidified with dilute HCL and filtered with suction, the phases were separated, the aqueous phase was extracted twice more with toluene, and the combined organic phases were washed with H2O, dried and concentrated. The crude product was taken up in 100 ml of methyl t-butyl ether and filtered with suction and cooling to remove precipitated triphenylphosphine oxide. The filtrate was concentrated and purified by column chromatography (silica gel, eluent: 98/2 methylene chloride/methanol); yield: 16.1 g (67%). Judging by a 1H-NMR spectrum, the styryl side chain is 90% in the trans configuration and 10% in the cis configuration.

Workup

  1. stirringstirred in at room temperature for 3 hours (color change toward pale yellow)
  2. filtrationfiltered with suction
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted twice more with toluene
  5. washthe combined organic phases were washed with H2O
  6. customdried
  7. concentrationconcentrated
  8. filtrationfiltered with suction
  9. temperaturecooling
  10. customto remove
  11. customprecipitated triphenylphosphine oxide
  12. concentrationThe filtrate was concentrated
  13. custompurified by column chromatography (silica gel, eluent: 98/2 methylene chloride/methanol)

Sources & evidence

ORD record
ord-1a5a594f36044658abb631379f496c6e
Source dataset
uspto-grants-1989_10
Patent number
US04877807

Reaction notes

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