Triethylsilane → 6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene

HRID 1453628Notes

Reaction equation

HRID 1453628 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:14])([CH3:13])[CH2:7][CH2:8][C:9]2=O)=[CH:4][CH:3]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5](=[CH:4][CH:3]=1)[C:6]([CH3:14])([CH3:13])[CH2:7][CH2:8][CH2:9]2

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 107533577-Bromo-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 105860636-Bromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthaleneYield 90%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 7-bromo-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one (prepared according to the procedures published in Journal of Medicinal Chemistry 1995, 38, 4764-7) (525 mg, 2.08 mmol) in 5 mL of trifluoroacetic acid (TFA) was added triethylsilane (2.41 g, 20.80 mmol). The mixture was then heated at reflux for 8 h. After cooling to room temperature, the reaction was quenched with 20 mL of ice-water mixture, extracted with diethyl ether (3×5 mL), washed with brine (1×5 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (hexane) afforded the title compound (445 mg, 90% yield) as a light yellow oil:

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 8 h
  3. customthe reaction was quenched with 20 mL of ice-water mixture
  4. extractionextracted with diethyl ether (3×5 mL)
  5. washwashed with brine (1×5 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated at reduced pressure
  8. customPurification by flash chromatography (hexane)

Sources & evidence

ORD record
ord-de3acb013ce647c29a33ebe39f596e3c
Source dataset
uspto-grants-2009_01
Patent number
US07476673B2

Reaction notes

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