Toluene → 3-Quinuclidyl alpha-Cyclopentyl-alpha-phenylethynylglycolate

HRID 358249Notes

Reaction equation

HRID 358249 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.[Na].C1(C)C=CC=CC=1.[CH:18]1([C:23]([C:30]#[C:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([OH:29])[C:24](OCC)=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19]1>CCCCCC>[CH:18]1([C:23]([C:30]#[C:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)([OH:29])[C:24]([O:9][CH:3]2[CH:4]3[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]3)[CH2:2]2)=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 15381(+-)-3-QuinuclidinolHCID 5360545Sodium2×HCID 54429989Ethyl alpha-cyclopentyl-alpha-phenylethynylglycolate

Product 1

HCID 133711473-Quinuclidyl alpha-Cyclopentyl-alpha-phenylethynylglycolate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

3-Quinuclidinol (3.8 g., 0.030 mole) and about 0.05 g. of sodium were refluxed in 50 ml. of toluene, in a flask equipped with a reflux head, until all the sodium reacted. Then, ethyl α-cyclopentyl-α-phenylethynylglycolate (5.4 g., 0.02 mole) in 35 ml. of solvent was added dropwise over an hour period. No temperature drop was noted in the reflux head. The reaction mixture was refluxed for about 18 hours and then about 40 ml. of solvent was distilled from the reaction flask over a four hour period. The reaction mixture was cooled, and dry 20°-40° petroleum ether was added. A tarry solid formed and was filtered. The solid was treated with hot hexane to yield 3.2 g. (45%) of crude product melting about 115° C. The pure compound, m.p. 137°-39°, was obtained by recrystallization from hexane.

Workup

  1. customreacted
  2. additionof solvent was added dropwise over an hour period
  3. temperatureThe reaction mixture was refluxed for about 18 hours
  4. distillationof solvent was distilled from the reaction flask over a four hour period
  5. temperatureThe reaction mixture was cooled
  6. dry with materialdry 20°-40° petroleum ether
  7. additionwas added
  8. customA tarry solid formed
  9. filtrationwas filtered
  10. additionThe solid was treated with hot hexane
  11. customto yield 3.2 g
  12. custommelting about 115° C

Sources & evidence

ORD record
ord-a5ffa85c4f634c8b88558d41d700b285
Source dataset
uspto-grants-1984_08
Patent number
US04465834

Reaction notes

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