Trifluoroacetic acid → HCID 54443836, compound

HRID 1038025Notes

Reaction equation

HRID 1038025 reaction equation
CO[CH2:3][N:4]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][Si](C)(C)C.FC(F)(F)C(O)=O.[CH2:24]([O:26][C:27](=[O:32])[C:28]([CH2:30][F:31])=[CH2:29])[CH3:25]>ClCCl>[CH2:24]([O:26][C:27]([C:28]1([CH2:30][F:31])[CH2:29][CH2:3][N:4]([CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:5]1)=[O:32])[CH3:25]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 12815505Ethyl 2-(fluoromethyl)prop-2-enoate

Product 1

HCID 54443836HCID 54443836, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (548 μl, 2.14 mmol) was dissolved in the dichloromethane solution of the 2-fluoromethyl-acrylic acid ethyl ester from the previous reaction and chilled to 0 C. A solution of trifluoroacetic acid (67 μl, 0.87 mmol) in dichloromethane (0.5 ml) was added slowly. The reaction mixture was allowed to warm to room temperature in two hours and directly chromatographed on silica gel. Elution with solutions of ethyl acetate in hexanes (1:5, 1:4, 1:3) obtained the title product (143 mg) as oil.

Workup

  1. temperaturechilled to 0 C
  2. customdirectly chromatographed on silica gel
  3. washElution with solutions of ethyl acetate in hexanes (1:5, 1:4, 1:3)

Sources & evidence

ORD record
ord-72185d25d4834282a8b8a0ca12e9e091
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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