Sodium Chloride → HCID 19036578, compound

HRID 264511Notes

Reaction equation

HRID 264511 reaction equation
C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[C:28](=[O:32])[CH2:27][CH2:26]2.Cl[CH2:34][C:35](=[O:37])[CH3:36].[Cl-].[Na+]>CCCCCC.O1CCCC1>[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[C:28](=[O:32])[CH:27]([CH2:34][C:35](=[O:37])[CH3:36])[CH2:26]2

Participants

9

Reactant 6

HCID 5234Sodium ChlorideHCID 6571ChloroacetoneHCID 7912DiisopropylamineHCID 787875-Methoxyindan-1-oneHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

Product 1

HCID 19036578HCID 19036578, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

A lithium diisopropylamide solution, freshly prepared from 4.25 ml of diisopropylamine and 18.7 ml of 1.6N n-butyllithium in hexane, in 60 ml of anhydrous tetrahydrofuran was added dropwise while stirring to a solution, cooled to -70°, of 3.24 g of 5-methoxy-1-indanone in 350 ml of anhydrous tetrahydrofuran. The mixture was stirred at this temperature for an additional 30 minutes and a solution of 1.6 ml of chloroacetone dissolved in 60 ml of anhydrous tetrahydrofuran was subsequently added dropwise over 15 minutes. The reaction mixture was left to come to room temperature over 100 minutes and was stirred at this temperature for an additional 45 minutes. Subsequently, the reaction mixture was poured on to 150 ml of ice, 150 ml of saturated sodium chloride were added and the organic phase was separated. The aqueous phase was extracted once with 400 ml of diethyl ether. The combined organic phases were washed once with 100 ml of saturated sodium chloride solution, dried over magnesium sulfate and concentrated in a vacuum. The red oil obtained was purified by column chromatography on silica gel (hexane/diethyl ether 3:7). There were obtained 1.67 g of crude product which was crystallized from diethyl ether/hexane. The crystallization gave 1.21 g (56%) of (RS)-5-methoxy-2-(2-oxopropyl)-1-indanone as a light yellow solid with m.p. 73°.

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred at this temperature for an additional 30 minutes
  3. additionwas subsequently added dropwise over 15 minutes
  4. waitThe reaction mixture was left
  5. stirringwas stirred at this temperature for an additional 45 minutes
  6. additionwere added
  7. customthe organic phase was separated
  8. extractionThe aqueous phase was extracted once with 400 ml of diethyl ether
  9. washThe combined organic phases were washed once with 100 ml of saturated sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated in a vacuum
  12. customThe red oil obtained
  13. customwas purified by column chromatography on silica gel (hexane/diethyl ether 3:7)
  14. customThere were obtained 1.67 g of crude product which
  15. customwas crystallized from diethyl ether/hexane
  16. customThe crystallization

Sources & evidence

ORD record
ord-53c9cdedd22d4402bce2103e0b94ac94
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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