Sodium Hydroxide → HCID 22600576, compound

HRID 1760084Notes

Reaction equation

HRID 1760084 reaction equation
[C:1]1([C:7]2[CH2:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:17][C:18]1[C:19]([CH2:24]Br)=[CH:20][CH:21]=[CH:22][CH:23]=1.[OH-].[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O1CCCC1>[C:1]1([C:7]2[C:8]3([CH2:24][C:19]4[C:18](=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:17]3)[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:15]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 66665o-Bis(bromomethyl)benzeneHCID 3534352-Phenyl-1H-indene

Product 1

HCID 22600576HCID 22600576, compound

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Benzyl trimethylammonium chloride (0.196 g, 1 mmol) was added to a solution of 2-phenylindene (0.200 g, 1.04 mmol) and α,α′-dibromoxylene (0.289 g, 1.09 mmol) in tetrahydrofuran (10 mL) then 50% aqueous sodium hydroxide (10 mL) was added. The resulting mixture was stirred at 50° C. overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed sequentially with water, 0.1 N hydrochloric acid, water, and saturated aqueous sodium chloride then dried (MgSO4), filtered, and evaporated to a yellow solid. The crude product was purified by preparative thin layer chromatography on silica gel eluted with 98:2 hexane:ethyl acetate to afford 2-phenyl-1′,3′-dihydro-spiro[1H-indene-1,2′-[2H]indene] as a white amorphous solid (0.048 g). NMR (CDCl3, 500 MHz) δ 7.56 (2H, d, J=7 Hz), 7.42 (1H, d, J=7 Hz), 7.24-7.38 (9H, m, ArH), 7.09 (1H, t, J=7 Hz, ArH), 7.02 (1H, d, J=7 Hz, ArH), 3.78 (2H, d, J=16.5 Hz, CH2), 3.19 (2H, d, J=16.5 Hz, CH2).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed sequentially with water, 0.1 N hydrochloric acid, water, and saturated aqueous sodium chloride
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to a yellow solid
  6. customThe crude product was purified by preparative thin layer chromatography on silica gel
  7. washeluted with 98:2 hexane

Sources & evidence

ORD record
ord-f57d7a34b8344a878893a0b6554f2be4
Source dataset
uspto-grants-2005_01
Patent number
US06838584B2

Reaction notes

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