tert-Butanol → 6-Bromo-2',3',5',6'-tetrahydrospiro[indene-2,4'-pyran]-1(3H)-one

HRID 472957Notes

Reaction equation

HRID 472957 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.C(O[K])(C)(C)C.CC(O)(C)C.Br[CH2:24][CH2:25][O:26][CH2:27][CH2:28]Br>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([C:8]2=[O:11])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 21521Bis(2-bromoethyl) etherHCID 1397781-Indanone, 6-bromo-HCID 178418922HCID 178418922, compound2×

Product 1

HCID 581981056-Bromo-2',3',5',6'-tetrahydrospiro[indene-2,4'-pyran]-1(3H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-1-indanone (1.033 g, 4.89 mmol) in anhydrous THF (100 mL) under N2 atmosphere at room temperature was added a solution of tBuOK in tBuOH (1 M, 10.3 mL, 10.3 mmol) within 30 min (the color turned to deep black upon a drop of tBuOK solution was added), followed by 1-bromo-2-(2-bromoethoxy)ethane (1.134 g, 0.62 mL, 4.89 mmol). The reaction was quenched with saturated aqueous NH4Cl, and extracted with ether two times. The combined organic phases were washed with H2O, brine, and dried over anhydrous Na2SO4, and filtered, and concentrated to give black tar. It was purified by flash chromatography on silica gel yield 300 mg of the desired product. MS ESI+ve m/z 281 (M+H)+.

Workup

  1. additionwas added),
  2. customThe reaction was quenched with saturated aqueous NH4Cl
  3. extractionextracted with ether two times
  4. washThe combined organic phases were washed with H2O, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give black tar
  9. customIt was purified by flash chromatography on silica gel yield 300 mg of the desired product

Sources & evidence

ORD record
ord-e3f40da7ccdd4f60bb700a6fa2f6cd10
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Reaction notes

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