Dimethyl Sulfoxide → HCID 19384695, compound

HRID 1633396Notes

Reaction equation

HRID 1633396 reaction equation
CS(C)=O.[CH3:5][O:6][C:7]([C:9]1(C(OC)=O)[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:18])[CH:15]=2)[CH2:10]1)=[O:8].O.[Cl-].[Li+]>CCOCC>[Cl:18][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH:9]([C:7]([O:6][CH3:5])=[O:8])[CH2:17]2

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 433294Lithium ChlorideHCID 204410142,2-Dimethoxycarbonyl-5-chloroindane

Product 1

HCID 19384695HCID 19384695, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 300 ml of dimethyl sulfoxide, were added successively 64.0 g of 2,2-dimethoxycarbonyl-5-chloroindane, 5 ml of water and 10 g of lithium chloride. The mixture was heated with stirring for 3 hours at 120° to 130° C. The reaction mixture was cooled to room temperature poured into 500 ml of ice water, and mixed with ether. After the ether layer was separated, the aqueous layer was extracted twice with ether. The ether layers were combined, washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a crude product. The crude product was distilled in vacuo to obtain 15.97 g of the purified intended product. Boiling point, 113°-131° C./0.3 mmHg.

Workup

  1. temperatureThe mixture was heated
  2. customAfter the ether layer was separated
  3. extractionthe aqueous layer was extracted twice with ether
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a crude product
  8. distillationThe crude product was distilled in vacuo

Sources & evidence

ORD record
ord-617d1998b66d423fa955b65dd9e094cc
Source dataset
uspto-grants-1984_10
Patent number
US04480118

Reaction notes

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