Tetrahydrofuran → 2-(Propan-2-ylidene)bicyclo[2.2.1]heptane

HRID 893531Notes

Reaction equation

HRID 893531 reaction equation
O1C[CH2:4][CH2:3][CH2:2]1.C[Mg]Br.C([C:12]12[CH2:18][CH:15]([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)(=O)C>C(OCC)C>[C:3](=[C:14]1[CH2:13][CH:12]2[CH2:18][CH:15]1[CH2:16][CH2:17]2)([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 1275750280606-49-1HCID 178418573HCID 178418573, compound

Product 1

HCID 126489212-(Propan-2-ylidene)bicyclo[2.2.1]heptane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Next, 1 L of tetrahydrofuran solution (concentration: approximately 2 mols/liter) of methylmagnesium bromide was placed in a three-liter four-necked flask, and the mixture of 260 g of acetyl norbornane obtained above and 500 ml of ethyl ether was added dropwise while stirred. After completion of the reaction, the reaction mixture was post treated by the ordinary method, and distilled, to obtain 210 g of isopropylidene norbornane with a purity of 90%.

Workup

  1. additionwas added dropwise
  2. customAfter completion of the reaction
  3. additiontreated by the ordinary method
  4. distillationdistilled

Sources & evidence

ORD record
ord-f3f0cd9bf74348d498e0c82e5fe28878
Source dataset
uspto-grants-1992_06
Patent number
US05126065

Reaction notes

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