5-hydroxy-8-methoxy-3,4-dihydro-2H-naphthalen-1-one → HCID 21255658, compound

HRID 636713Notes

Reaction equation

HRID 636713 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=O>FC(F)(F)C(O)=O>[CH3:13][O:12][C:9]1[C:8]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=2[C:2]([OH:1])=[CH:11][CH:10]=1

Participants

3

Reactant 1

HCID 109978555-hydroxy-8-methoxy-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 21255658HCID 21255658, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of 5-hydroxy-8-methoxy-3,4-dihydro-2H-naphthalen-1-one (1.7 g) in trifluoroacetic acid (20 mL) triethylsilane (4.2 mL) was added and the reaction warmed to RT and then stirred for 1.5 h). The reaction mixture was concentrated in vacuo, partitioned between ethyl acetate/water, the organic layer was washed with water, brine, and then dried over sodium sulfate and concentrated in vacuo. The resulting oil is flash chromatographed (10% ethyl acetate/hexanes) to afford the title compound as a colorless solid (1.6 g).

Workup

  1. additionwas added
  2. temperaturethe reaction warmed to RT
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompartitioned between ethyl acetate/water
  5. washthe organic layer was washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customchromatographed (10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6176022d31614c67844137558d757a14
Source dataset
uspto-grants-2001_02
Patent number
US06194454B1

Reaction notes

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