Trifluoroacetic acid → HCID 131727570, compound

HRID 2100591Notes

Reaction equation

HRID 2100591 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([CH2:13][CH2:14][CH3:15])[CH:10]=[C:9](/[CH:16]=[CH:17]/[C:18]([O:20][CH3:21])=[O:19])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].CO[CH2:24][N:25]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:26][Si](C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.FC(F)(F)C(O)=O>[CH2:31]([N:25]1[CH2:26][C@@H:16]([C:9]2[CH:10]=[C:11]([CH2:13][CH2:14][CH3:15])[CH:12]=[C:2]([Cl:1])[C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C@H:17]([C:18]([O:20][CH3:21])=[O:19])[CH2:24]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine2×HCID 131727569HCID 131727569, compound

Product 1

HCID 131727570HCID 131727570, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (E)-ethyl 2-chloro-6-(3-methoxy-3-oxoprop-1-enyl)-4-propylbenzoate (0.92 g, 2.96 mmol) in 20 mL of CH2Cl2 was added N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (0.77 g, 3.25 mmol) and trifluoroacetic acid (0.045 mL, 0.6 mmol). The solution was allowed to stir at 40° C. for 2 h. Starting material still remained by TLC analysis and so additional N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (0.1 g, 0.4 mmol) and trifluoroacetic acid (2 drops) were added and the reaction was stirred at 40° C. for an additional 30 min and then at ambient temperature for 18 h. The reaction was quenched with sat'd aq NaHCO3 and extracted with EtOAc. The organics were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (230-400 mesh silica gel, 6:1 hexane/EtOAc) to afford 1.17 g (90%) of the title compound as an oil. LRMS (ES)+: 444.25/446.24 (M+H)+.

Workup

  1. additionwere added
  2. stirringthe reaction was stirred at 40° C. for an additional 30 min
  3. waitat ambient temperature for 18 h
  4. customThe reaction was quenched with sat'd aq NaHCO3
  5. extractionextracted with EtOAc
  6. washThe organics were washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (230-400 mesh silica gel, 6:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-def9cbcf54b34aa292c275cb11fe975d
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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