HCID 178418255, compound → 1,2,3,5-Tetrahydro-7-phenyl-s-indacene

HRID 1060512Notes

Reaction equation

HRID 1060512 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(OCC)C>[C:1]1([C:2]2[C:2]3[CH:3]=[C:4]4[C:5]([CH2:3][CH2:4][CH2:5]4)=[CH:6][C:1]=3[CH2:6][CH:1]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 178418255HCID 178418255, compound

Product 1

HCID 186283771,2,3,5-Tetrahydro-7-phenyl-s-indaceneYield 180.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3,5,6,7-Tetrahydro-s-Hydrindacen-1(2H)-one (12.00 g, 0.06967 moles) was stirred in diethylether (200 mL) at 0° C. as PhMgBr (0.105 moles, 35.00 mL of 3.0 M solution in diethylether) was added slowly. This mixture was then allowed to stir overnight at room temperature. After the reaction period the mixture was quenched by pouring over ice. The mixture was then acidified (pH=1) with HCl and stirred vigorously for 2 hours. The organic layer was then separated and washed with H2O (2×100 mL) and then dried over MgSO4. Filtration followed by the removal of the volatiles resulted in the isolation of the desired product as a dark oil (14.68 g, 90.3% yield).

Workup

  1. additionwas added slowly
  2. customAfter the reaction period the mixture
  3. customwas quenched
  4. additionby pouring over ice
  5. stirringstirred vigorously for 2 hours
  6. customThe organic layer was then separated
  7. washwashed with H2O (2×100 mL)
  8. dry with materialdried over MgSO4
  9. filtrationFiltration
  10. customfollowed by the removal of the volatiles

Sources & evidence

ORD record
ord-b3fc29d70cff46b6b359821a808fadb6
Source dataset
uspto-grants-2003_02
Patent number
US06524702B1

Reaction notes

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