Hexane → HCID 11805008, compound

HRID 888322Notes

Reaction equation

HRID 888322 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.C([Li])CCC.CCCCCC.[NH4+].[Cl-]>C(O)(C)C>[CH2:7]1[C:6]2[C:10](=[CH:11][C:12]3[CH2:1][CH:2]=[CH:3][C:4]=3[CH:5]=2)[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 109318913,5,6,7-tetrahydro-s-indacen-1(2H)-oneHCID 178418339Butyllithium

Product 1

HCID 11805008HCID 11805008, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The mixture of 3,5,6,7-tetrahydro-s-indacen-1(2H)-one (12.4 g, 0.072 mol), p-toluenesulfonyl hydrazide (13.4 g, 0.072 mol), 0.5 g TSA and i-propanol (100 ml) was refluxed by 5 min, and cooled to room temperature. Precipitate was filtered, washed by MeOH and dried, given 21 g of product (90%). Suspension of obtained hydrazone in 250 ml abs. Et2O was cooled to −70° C. and was treated with 15% n-butyllithium in hexane (100 ml. 0.16 mol). The resulting mixture was allowed to warm up to r.t. and refluxed until gas evolution. Reaction mixture was treated with 50 ml NH4Cl (10%), washed by water and dried. Solvent was evaporated, the residue was extracted by hot hexane, and to give after evaporation 9.1 g of solid product (81%).

Workup

  1. temperaturewas refluxed by 5 min
  2. filtrationPrecipitate was filtered
  3. washwashed by MeOH
  4. customdried
  5. additionSuspension of obtained hydrazone in 250 ml abs
  6. temperatureEt2O was cooled to −70° C.
  7. temperatureto warm up to r.t.
  8. temperaturerefluxed until gas evolution
  9. customReaction mixture
  10. washwashed by water
  11. customdried
  12. customSolvent was evaporated
  13. extractionthe residue was extracted by hot hexane
  14. customto give
  15. customafter evaporation 9.1 g of solid product (81%)

Sources & evidence

ORD record
ord-1158f6394c2f40158f4c24daaae87586
Source dataset
uspto-grants-2012_08
Patent number
US08247587B2

Reaction notes

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