Water → (2-Ethenylcyclopropane-1,1-diyl)dimethanol

HRID 1723038Notes

Reaction equation

HRID 1723038 reaction equation
[CH:1]([CH:3]1[CH2:5][C:4]1([C:11](OCC)=[O:12])[C:6](OCC)=[O:7])=[CH2:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1.C1CCCCC1.C(OCC)(=O)C>[OH:7][CH2:6][C:4]1([CH2:11][OH:12])[CH2:5][CH:3]1[CH:1]=[CH2:2]

Participants

6

Reactant 3

HCID 962WaterHCID 111025Diethyl 2-vinylcyclopropane-1,1-dicarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 13572991(2-Ethenylcyclopropane-1,1-diyl)dimethanolYield 93.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21867204Cyclohexane ethylacetateSolvent

Procedure

A solution of 23 g (0.108 mole) of diethyl 2-vinylcyclopropane-1,1-dicarboxylate in 90 ml of dry THF (tetrahydrofuran) was added dropwise to 196 ml of 1M LAH (lithium aluminum hydride) which was stirred and heated at 68°. The addition required 30 minutes and heating and stirring were continued for 2 hours. TLC in cyclohexane-ethyl acetate (1:1) and CHCl3MeOH (9:1) showed that the reaction was complete. The reaction was cooled to 0° and a total of 200 ml of water was continuously added. After being stirred for 15 minutes, the mixture was filtered and the solid was washed with THF. The combined filtrates were concentrated to yield 12.9 g (93%) of the title compound, RfCHCl3 -MeOH (9:1) 0.45.

Workup

  1. temperatureheated at 68°
  2. additionThe addition required 30 minutes
  3. temperatureheating
  4. stirringstirring
  5. temperatureThe reaction was cooled to 0°
  6. stirringAfter being stirred for 15 minutes
  7. filtrationthe mixture was filtered
  8. washthe solid was washed with THF
  9. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-3fae9dbf643a416c9e85befe51e8b204
Source dataset
uspto-grants-1989_08
Patent number
US04859680

Reaction notes

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