Sulfuric Acid → HCID 20188223, compound

HRID 1789402Notes

Reaction equation

HRID 1789402 reaction equation
[Mg].Br[CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.N1(N[C:19](=[O:27])[CH:20]([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23])CCCCC1.S(=O)(=O)(O)O>C(OCC)C>[CH2:22]([O:21][C:20]([O:24][CH2:25][CH3:26])([CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1)[CH:19]=[O:27])[CH3:23]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 5462224Magnesium2×HCID 109654632-bromo-2,3-dihydro-1H-indeneHCID 54475451HCID 54475451, compound

Product 1

HCID 20188223HCID 20188223, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

0.73 g of magnesium turnings are covered with 90 ml of dry diethylether. To that mixture is then added 6 g of 2-bromoindane in 20 ml of dry diethylether at such a rate that a gentle boiling is maintained. When the magnesium turnings have reacted the solution containing the Grignard reagent is cooled to room temperature. The reaction mixture is then added dropwise, over a period of 3 hours, to a cooled (0°-5° C. solution of diethoxyacetic acid piperidinyl amide (6.4 g) in 20 ml of dry diethylether. After the addition is complete, the reaction mixture is stirred for two hours at about 5° C. The mixture is then poured into a cold 2% sulfuric acid solution (50 ml). The solution is extracted with ether and the combined ether extracts are washed with water and evaporated to dryness to give a residue of crude product, which is used without purification in step (b).

Workup

  1. temperatureis maintained
  2. additionThe reaction mixture is then added dropwise, over a period of 3 hours
  3. additionAfter the addition
  4. extractionThe solution is extracted with ether
  5. washthe combined ether extracts are washed with water
  6. customevaporated to dryness
  7. customto give a residue of crude product, which
  8. customis used without purification in step (b)

Sources & evidence

ORD record
ord-e661ba1483df42c9a16946f9259de1b6
Source dataset
uspto-grants-1987_08
Patent number
US04689339

Reaction notes

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