Acetone → HCID 20441018, compound

HRID 1633399Notes

Reaction equation

HRID 1633399 reaction equation
C([N-]C(C)C)(C)C.[Li+].C([Li])CCC.C(NC(C)C)(C)C.[CH2:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH:22]1[C:30]([O:32][CH3:33])=[O:31].[CH3:34][C:35]([CH3:37])=[O:36]>C1COCC1>[OH:36][C:35]([C:22]1([C:30]([O:32][CH3:33])=[O:31])[CH2:21][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23]1)([CH3:37])[CH3:34]

Participants

7

Reactant 5

HCID 180AcetoneHCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 9964238Methyl indane-2-carboxylateHCID 178418339Butyllithium

Product 1

HCID 20441018HCID 20441018, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-50 °C

Procedure

To a dried THF solution of lithiumdiisopropylamide prepared from 107.3 ml (0.149 mole) of n-butyllithium and 15.81 g (0.156 mole) of diisopropylamine, was added dropwise at -50° C. a solution of 25.0 g (0.142 mole) of methyl indane-2-carboxylate in 50 ml of dried THF over a period of 10 minutes. To the resulting mixture, which had been stirred for 30 minutes at -50° C., was added dropwise over a period of 10 minutes a solution of 9.88 g (0.17 mole) of dried acetone in 10 ml of dried THF. After the addition, stirring was continued for further 10 minutes. The reaction mixture was poured into ice water and extracted with ether. The aqueous layer was extracted twice with ether. The ether layers were combined, washed successively with 3% aqueous hydrochloric acid solution, saturated aqueous hydrogen-carbonate solution, and saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain the intended product as a oily substance.

Workup

  1. additionAfter the addition
  2. stirringstirring
  3. waitwas continued for further 10 minutes
  4. extractionextracted with ether
  5. extractionThe aqueous layer was extracted twice with ether
  6. washwashed successively with 3% aqueous hydrochloric acid solution, saturated aqueous hydrogen-carbonate solution, and saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto obtain the intended product as a oily substance

Sources & evidence

ORD record
ord-3a2dca6278324092a6fa6e09fe6780f0
Source dataset
uspto-grants-1984_10
Patent number
US04480118

Reaction notes

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