Trifluoroacetic acid → HCID 86087052, compound

HRID 1992991Notes

Reaction equation

HRID 1992991 reaction equation
O[C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)[C:5](=[O:6])[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=2)=[C:3]1[CH3:15].C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:15][C:3]1[CH:2]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)[C:5](=[O:6])[C:4]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86087051HCID 86087051, compound

Product 1

HCID 86087052HCID 86087052, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A CH2Cl2 solution (15 mL) of 4-hydroxy-3-methyl-2,4-bis[3-(methyloxy)phenyl]-2-cyclobuten-1-one (246) (0.464 g, 1.50 mmol, 1 equiv) was cooled to ca. 0° C. Triethylsilane (3.02 mL, 1.0 M, 1.5 equiv) was added followed by TFA. After 5 min, the ice bath was removed and the reaction was allowed to warm to ambient temperature. After an additional 2 h, the reaction was quenched with 50% saturated aqueous NaHCO3. The organic portion was separated and pooled with those extracted using EtOAc (3×20 mL). The organic portions were dried (Na2SO4), filtered, and concentrated. Radial chromatography (SiO2, 2 mm plate, 80:20; hexanes/EtOAc) afforded the title compound as a yellow oil (0.374 g, 85%). 1H NMR (CDCl3, 300 MHz) δ 7.38-7.30 (m, 4H), 6.96-6.80 (m, 4H), 4.69 (s, 1H), 3.89 (s, 3H), 3.83 (s, 3H), 2.49 (s, 3H). TLC (80:20; hexanes/EtOAc): Rf=0.46.

Workup

  1. customthe ice bath was removed
  2. waitAfter an additional 2 h
  3. customthe reaction was quenched with 50% saturated aqueous NaHCO3
  4. customThe organic portion was separated
  5. dry with materialThe organic portions were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0c46bab6fdaf4e4cacee831dcbaaba69
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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