Water → HCID 22218293, compound

HRID 1453633Notes

Reaction equation

HRID 1453633 reaction equation
C[Mg]Br.[Br:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=O)[CH2:10][CH2:9][C:8]2([CH3:17])[CH3:16].[C:18]1(C)C=CC(S(O)(=O)=O)=CC=1.O>C(OCC)C.ClCCl>[Br:4][C:5]1[CH:6]=[C:7]2[C:12]([C:11]([CH3:18])=[CH:10][CH2:9][C:8]2([CH3:17])[CH3:16])=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 118319356-Bromo-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one2×HCID 178418573HCID 178418573, compound

Product 1

HCID 22218293HCID 22218293, compoundYield 403.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl magnesium bromide (3M solution in diethyl ether, 2.5 mL, 7.50 mmol) was added slowly to a solution of 6-bromo-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one (Compound 35, 920 mg, 3.65 mmol) in 10 mL of diethyl ether at 0° C. After stirring and warming to room temperature for 2 h, the mixture was quenched with water at 0° C., extracted with diethyl ether (3×5 mL), washed with brine (1×5 mL), dried (MgSO4) and concentrated at reduced pressure to give a light yellow oil. The crude oil was then dissolved in 10 mL of dichloromethane and stirred with 100 mg of para-toluenesulfonic acid at room temperature for 2 h. Water (10 mL) was then added and the organic layer was washed with brine (1×5 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (hexane) gave the title compound (589 mg, 65% yield) as a colorless oil:

Workup

  1. customthe mixture was quenched with water at 0° C.
  2. extractionextracted with diethyl ether (3×5 mL)
  3. washwashed with brine (1×5 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated at reduced pressure
  6. customto give a light yellow oil
  7. washthe organic layer was washed with brine (1×5 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated at reduced pressure
  10. customPurification by flash chromatography (hexane)

Sources & evidence

ORD record
ord-d943f0efdeff49c8bef9b6bc1ce32b86
Source dataset
uspto-grants-2009_01
Patent number
US07476673B2

Reaction notes

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