Cyclopentadiene → 2-Methyladamantan-2-yl bicyclo[2.2.1]hept-5-ene-2-carboxylate

HRID 325122Notes

Reaction equation

HRID 325122 reaction equation
[C:1]([O:5][C:6]1([CH3:16])[CH:13]2[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:15][CH:7]1[CH2:8]3)[CH2:12]2)(=[O:4])[CH:2]=[CH2:3].[CH:17]1[CH2:21][CH:20]=[CH:19]C=1.[CH2:22]1COCC1>>[CH:3]12[CH2:22][CH:21]([CH:20]=[CH:19]1)[CH2:17][CH:2]2[C:1]([O:5][C:6]1([CH3:16])[CH:7]2[CH2:15][CH:11]3[CH2:10][CH:9]([CH2:14][CH:13]1[CH2:12]3)[CH2:8]2)=[O:4]

Participants

4

Reactant 3

HCID 7612CyclopentadieneHCID 8028Tetrahydrofuran2×HCID 112182922-Methyladamantan-2-yl Acrylate (stabilized with MEHQ)

Product 1

HCID 154779042-Methyladamantan-2-yl bicyclo[2.2.1]hept-5-ene-2-carboxylate

Conditions

Temperature
50 °C

Procedure

20 2-methyl-2-adamantyl acrylate (44 g, 0.2 mol) was dissolved in 250 ml of THF, cyclopentadiene (20 g, 0.3 mol) was added slowly thereto at 0° C. and then the reaction temperature was raised to about 50° C. Then, the reaction was stirred for about 20 hours. After completion of the reaction, excess THF was removed using a rotary evaporator and then neutralized with dilute sulfuric acid. Then, the resultant product was extracted using diethyl ether and dried over magnesium sulfate. The obtained crude product was vacuum-distilled to yield the desired compound of viscous colorless liquid (yield: 90%) FIGS. 1 and 2 are NMR and FT-IR spectrums of the compound.

Workup

  1. customwas removed
  2. customa rotary evaporator
  3. extractionThen, the resultant product was extracted
  4. dry with materialdried over magnesium sulfate
  5. customThe obtained crude product
  6. distillationwas vacuum-distilled

Sources & evidence

ORD record
ord-a7639953d9894f59beb4fd43486e4156
Source dataset
uspto-grants-2001_04
Patent number
US06222061B1

Reaction notes

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