Trifluoroacetic acid → HCID 68459898, compound

HRID 502617Notes

Reaction equation

HRID 502617 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:14](O)([CH3:16])[CH3:15])=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][CH:10]([CH3:13])[C:11]=2[CH:12]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:14]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[O:2][CH3:1])[CH:10]([CH3:13])[CH2:9][CH2:8][CH2:7]2)([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68458169HCID 68458169, compound

Product 1

HCID 68459898HCID 68459898, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(3-methoxy-5-methyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-2-ol (5.38 g, 22.96 mmol) in methylene chloride (100 mL) at room temperature under nitrogen atmosphere, was added triethyl silane (36.6 mL, 229.6 mmol) followed by trifluoroacetic acid (17.7 mL, 229.6 mmol). The reaction mixture was stirred for five hours at room temperature, then was concentrated under reduced pressure. The residue was partitioned between methylene chloride and saturated aqueous potassium carbonate solution. The organic layer was separated, washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified with flash chromatography on silica (10:0.1 hexanes/dichloromethane) to give 3.06 g of 6-isopropyl-7-methoxy-1-methyl-1,2,3,4-tetrahydro-naphthalene.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe residue was partitioned between methylene chloride and saturated aqueous potassium carbonate solution
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified with flash chromatography on silica (10:0.1 hexanes/dichloromethane)

Sources & evidence

ORD record
ord-6027d7f84b7e4d77bf8f97723370324f
Source dataset
uspto-grants-2010_08
Patent number
US07776872B2

Reaction notes

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