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

HRID 1525744Notes

Reaction equation

HRID 1525744 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-0d896fe2f7784e79b4a61df0dbca686d
Source dataset
uspto-grants-2015_07
Patent number
US09085534B2

Reaction notes

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