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

HRID 63090Notes

Reaction equation

HRID 63090 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 C11H11FO2, 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-db2e70e06ffa4211ab8ab64968b3a57e
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Reaction notes

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