Methyl phenylacetate → Methyl 2-(1-benzylpyrrolidin-2-ylidene)(phenyl)acetate

HRID 2099585Notes

Reaction equation

HRID 2099585 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[C:11]1([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.F[B-](F)(F)F.[CH2:27]([N+:34]1[CH2:35][CH2:36][CH2:37][C:38]=1OCC)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O1CCCC1>[CH2:27]([N:34]1[CH2:35][CH2:36][CH2:37][C:38]1=[C:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:18]([O:20][CH3:21])=[O:19])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7559Methyl phenylacetateHCID 2733832Lithium HexamethyldisilazideHCID 866029921-benzyl-5-ethoxy-3,4-dihydro-2H-pyrrolium tetrafluoroborate

Product 1

HCID 68800975Methyl 2-(1-benzylpyrrolidin-2-ylidene)(phenyl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Lithium hexamethyldisilazide solution (8.39 mL of 1M in tetrahydrofuran, 8.39 mmol) was added to dry THF and cooled to −78° C. Methyl phenylacetate (1.15 mL, 7.99 mmol) was added dropwise, and the reaction stirred for 15 minutes. A solution of 1-benzyl-5-ethoxy-3,4-dihydro-2H-pyrrolium tetrafluoroborate in 5 mL of tetrahydrofuran was added dropwise, and after one hour the reaction was allowed to warm to room temperature. The mixture was quenched with saturated NaHCO3 solution, warmed to ambient temperature and poured into water. The aqueous layer was extracted with EtOAc and the organic extract was washed with brine, dried with Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (25-30% EtOAc/hexane), providing methyl 2-(1-benzylpyrrolidin-2-ylidene)(phenyl)acetate. ESI+MS: 308.3 [M+H]+.

Workup

  1. waitafter one hour the reaction was allowed
  2. temperatureto warm to room temperature
  3. customThe mixture was quenched with saturated NaHCO3 solution
  4. temperaturewarmed to ambient temperature
  5. additionpoured into water
  6. extractionThe aqueous layer was extracted with EtOAc
  7. extractionthe organic extract
  8. washwas washed with brine
  9. dry with materialdried with Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by silica gel chromatography (25-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-df6d0ed43c554512bdff51d82061937b
Source dataset
uspto-grants-2009_08
Patent number
US07569589B2

Reaction notes

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