Trifluoroacetic acid → HCID 131728353, compound

HRID 1038013Notes

Reaction equation

HRID 1038013 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]([C:7]([CH3:15])([CH3:14])[O:8][SiH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH2:6])[CH3:2].CO[CH2:19][N:20]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:21][Si](C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:3][C:4]([C:5]1([C:7]([CH3:15])([CH3:14])[O:8][SiH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:6][CH2:19][N:20]([CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:21]1)=[O:16])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 131728354HCID 131728354, compound

Product 1

HCID 131728353HCID 131728353, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold solution of 2-(tert-butyl-dimethyl-silanyloxymethyl)-acrylic acid ethyl ester (463 mg, 1.89 mmol) and N-(methoxymethyl)-N-(trimethylsilylmethyl)benzyl-amine (540 μl, 2.11 mmol) in dichloromethane (3 ml) was added at 0° C. trifluoroacetic acid (26 μl, 0.34 mmol). The resulting solution was warmed to room temperature in two hours. The crude product was purified by column chromatography on silica get eluting with a solution of ethyl acetate in hexanes (1:10, 1:5) to give the title compound (490 mg, 69%).

Workup

  1. customThe crude product was purified by column chromatography on silica
  2. customget
  3. washeluting with a solution of ethyl acetate in hexanes (1:10, 1:5)

Sources & evidence

ORD record
ord-b1b4951f54464cf7b4b79ad3d01895f1
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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