Trifluoroacetic acid → (3-Chloro-2-hydroxyphenyl)(2-methoxyphenyl)methane

HRID 1111279Notes

Reaction equation

HRID 1111279 reaction equation
[Cl:1][C:2]1[C:3]([O:18]COC)=[C:4]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])O)[CH:5]=[CH:6][CH:7]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:3]([OH:18])=[C:4]([CH2:8][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 15679047(3-Chloro-2-methoxymethoxyphenyl)(2-methoxyphenyl)methanol

Product 1

HCID 22151939(3-Chloro-2-hydroxyphenyl)(2-methoxyphenyl)methane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(3-Chloro-2-methoxymethoxyphenyl)(2-methoxyphenyl)methanol (15.27 g, 49 mmol) was combined with 15.97 g (100 mmol) of triethylsilane in 150 ml of methylene chloride and to this was added at ambient temperature with stirring under nitrogen 14.8 g (130 mmol) of trifluoroacetic acid. The mixture was stirred for 4 hours and was then poured into saturated aqueous sodium bicarbonate. Additional methylene chloride was added and the organic phase was recovered, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The residue was purified by preparative liquid chromatography eluting with a 1:99 mixture of acetone and hexane to obtain 3.98 g (33 percent of theory) of the title compound. The proton nmr spectrum was consistent with the assigned structure.

Workup

  1. additionto this was added at ambient temperature
  2. stirringThe mixture was stirred for 4 hours
  3. customthe organic phase was recovered
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe residue was purified by preparative liquid chromatography
  7. washeluting with a 1:99 mixture of acetone and hexane

Sources & evidence

ORD record
ord-cf27ebe0a129414a94835b5209ea9b65
Source dataset
uspto-grants-1990_12
Patent number
US04979978

Reaction notes

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