Hydrochloric Acid → 1,2,3,5,6,7-Hexahydro-s-indacene

HRID 2303593Notes

Reaction equation

HRID 2303593 reaction equation
[C:1]1(=O)[C:12]2[C:4](=[CH:5][C:6]3[CH2:7][CH2:8][CH2:9][C:10]=3[CH:11]=2)[CH2:3][CH2:2]1.Cl.[H][H]>[Pd].C(O)C>[CH2:3]1[C:4]2[C:12](=[CH:11][C:10]3[CH2:9][CH2:8][CH2:7][C:6]=3[CH:5]=2)[CH2:1][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 109318913,5,6,7-tetrahydro-s-indacen-1(2H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 1363211,2,3,5,6,7-Hexahydro-s-indaceneYield 73.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3,5,6,7-tetrahydro-2H-s-indacen-1-one (90 grams), ethanol (1 L), 10% palladium on carbon (1-2 grams) and concentrated hydrochloric acid (50 mL) was hydrogenated on a Parr shaker at room temperature until hydrogen uptake ceased. The mixture was filtered through a Celite pad. The pad was washed with 1 L diethyl ether. The filtrate was diluted with water and the organic phase was separated. The aqueous phase was extracted with 1 L of ether, and the combined ether extracts were washed with water, saturated sodium bicarbonate solution and brine. The ether extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting pale yellow solid was recrystallized from methanol to afford 61 grams of the title compound as colorless crystals, m.p. 56.6-58.5° C.

Workup

  1. filtrationThe mixture was filtered through a Celite pad
  2. washThe pad was washed with 1 L diethyl ether
  3. additionThe filtrate was diluted with water
  4. customthe organic phase was separated
  5. extractionThe aqueous phase was extracted with 1 L of ether
  6. washthe combined ether extracts were washed with water, saturated sodium bicarbonate solution and brine
  7. dry with materialThe ether extracts were dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe resulting pale yellow solid was recrystallized from methanol

Sources & evidence

ORD record
ord-5bd5db42684f4dbcbad18e4ce0f08c23
Source dataset
uspto-grants-2002_08
Patent number
US06433009B1

Reaction notes

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