L-Proline → HCID 11116496, compound

HRID 2226683Notes

Reaction equation

HRID 2226683 reaction equation
[Li]CCCC.N1CCC[C@H]1C(O)=O.[CH3:14][C:15]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[C:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1>CCOCC>[C:21]1([CH:15]([C:16]2[CH2:20][CH:19]=[CH:18][CH:17]=2)[CH3:14])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 5928226-Methyl-6-phenylfulveneHCID 178418339Butyllithium

Product 1

HCID 11116496HCID 11116496, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

n-BuLi (15 mL, 1.6M in hexanes, 24 mmol) was added dropwise to 1.4 g (12 mmol) of L-proline in 40 mL of ether. The resulting suspension was allowed to stir at room temperature over night. The reaction mixture was cooled to -78° C. and 2.0 g (12 mmol) of 6-methyl-6-phenylfulvene added dropwise. The reaction mixture was stirred at -78° C. for eight hours. The reaction mixture was allowed to warm to room temperature and the organic and aqueous layers were separated. The organic layer was dried over MgSO4 and the solvent removed under vacuum to give 2.05 g (100% yield) of (1-phenylethyl)cyclopentadiene as a yellow oil. The product was found to have a specific rotation of 4°(12% ee) .

Workup

  1. temperatureThe reaction mixture was cooled to -78° C.
  2. stirringThe reaction mixture was stirred at -78° C. for eight hours
  3. temperatureto warm to room temperature
  4. customthe organic and aqueous layers were separated
  5. dry with materialThe organic layer was dried over MgSO4
  6. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-a1f3aece6e4b495a9ccd96bce60840c4
Source dataset
uspto-grants-1994_09
Patent number
US05349100

Reaction notes

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