6-Methoxy-alpha-tetralone → 88288-05-5

HRID 1847197Notes

Reaction equation

HRID 1847197 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.[B-](F)(F)(F)[F:15].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C>[F:15][C:4]1[C:3]([O:2][CH3:1])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH2:8][C:9]2=[O:13]

Participants

4

Reactant 2

HCID 141126-Methoxy-alpha-tetraloneHCID 2724933Selectfluor

Product 1

HCID 1316604788288-05-5Yield 42.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 6-methoxy-1-tetralone (200 mg, 1.1 mmol) in ACN (20 mL) was added Selectfluor (603 mg, 1.7 mmol) at rt, and the reaction was stirred at 40° C. overnight. The reaction was filtered and concentrated. The residue was dissolved in EtOAc (40 mL), filtered, and concentrated. Purification by silica gel chromatography (PE/EtOAc/DCM=20:1:2) gave 90 mg (41%) of the title compound as a yellow solid. [M+H] Calc'd for C11H1FO2, 195. Found, 195.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOAc (40 mL)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (PE/EtOAc/DCM=20:1:2)

Sources & evidence

ORD record
ord-de9d0878fbfe4a248cb2f91b5feb0aa8
Source dataset
uspto-grants-2015_02
Patent number
US08952151B2

Reaction notes

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