Trifluoroacetic acid → HCID 131727576, compound

HRID 2100636Notes

Reaction equation

HRID 2100636 reaction equation
[CH3:1][O:2][C:3](=[O:20])/[CH:4]=[CH:5]/[C:6]1[C:7]([C:16]([O:18][CH3:19])=[O:17])=[CH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2.FC(F)(F)C(O)=O.CO[CH2:30][N:31]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:32][Si](C)(C)C>C(Cl)Cl>[CH2:37]([N:31]1[CH2:32][C@@H:5]([C:6]2[C:7]([C:16]([O:18][CH3:19])=[O:17])=[CH:8][C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:15]=2)[C@H:4]([C:3]([O:2][CH3:1])=[O:20])[CH2:30]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 11601463HCID 11601463, compound

Product 1

HCID 131727576HCID 131727576, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-methyl 3-(3-methoxy-3-oxoprop-1-enyl)-2-naphthoate (1.65 g, 6.09 mmol) in 15 mL of methylene chloride was added trifluoroacetic acid (0.07 mL, 0.91 mmol) and N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (2.34 mL, 9.13 mmol). The reaction mixture was allowed to stir at ambient temperature for 18 h. The solution was concentrated in vacuo and purified (ISCO, elution with 0-25% EtOAc/hexane) to afford 2.1 g (86%) of the title compound as an oil. 1H NMR (CDCl3): δ 8.34 (s, 1H), 8.15 (s, 1H), 7.87-7.80 (m, 2H), 7.58-7.53 (m, 1H), 7.50-7.41 (m, 3H), 7.39-7.33 (m, 2H), 7.30-7.25 (m, 1H), 4.57-4.51 (m, 1H), 3.94 (s, 3H), 3.74 (ABq, 2H), 3.68 (s, 3H), 3.36-3.31 (m, 1H), 3.27-3.20 (m, 1H), 3.07-3.02 (m, 2H), 2.80-2.75 (m, 1H). LRMS (ESI): 404.0 (M+H)+.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. custompurified
  3. wash(ISCO, elution with 0-25% EtOAc/hexane)

Sources & evidence

ORD record
ord-b4c73641236d47c793b0bdfaba1175c4
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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