Trifluoroacetic acid → HCID 68463403, compound

HRID 502621Notes

Reaction equation

HRID 502621 reaction equation
O[C:2]([C:5]1[C:6]([OH:17])=[CH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH3:16])=[CH:10][CH:9]=2)([CH3:4])[CH3:3].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[CH:2]([C:5]1[C:6]([OH:17])=[CH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH3:16])=[CH:10][CH:9]=2)([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68458034HCID 68458034, compound

Product 1

HCID 68463403HCID 68463403, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 3-(1-hydroxy-1-methyl-ethyl)-6-methoxy-naphthalen-2-ol (2.4 g, 10.33 mmol) in 50 mL dichloromethane at room temperature under nitrogen atmosphere, was added triethyl silane (16.5 mL, 103.3 mmol) followed by trifluoroacetic acid (7.96 mL, 103.3 mmol). The reaction mixture was stirred for 40 minutes, after which solvent was removed under reduced pressure. The residue was partitioned between dichloromethane and saturated aqueous potassium carbonate solution. The organic layer was washed with water and brine, dried (Na2SO4), filtered and concentrated under reduced pressure to give 1.2 g of 3-isopropyl-6-methoxy-naphthalen-2-ol as an oil.

Workup

  1. customafter which solvent was removed under reduced pressure
  2. customThe residue was partitioned between dichloromethane and saturated aqueous potassium carbonate solution
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-173d1e1db2ff42418272c0fd395de31a
Source dataset
uspto-grants-2010_08
Patent number
US07776872B2

Reaction notes

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