Trifluoroacetic acid → HCID 1515311, compound

HRID 626942Notes

Reaction equation

HRID 626942 reaction equation
[CH2:1]([N:8]([CH2:14]OC)[CH2:9][Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:22][CH2:23][CH3:24])(=[O:21])[C:18]#[C:19][CH3:20].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([N:8]1[CH2:9][C:19]([CH3:20])=[C:18]([C:17]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 78043Ethyl 2-butynoateHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine

Product 1

HCID 1515311HCID 1515311, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Benzyl(methoxymethyl)[(trimethylsilyl)methyl]amine (10.78 mL, 42.12 mmol) and ethyl but-2-ynoate (5.89 mL, 50.54 mmol) were stirred in DCM (500 mL) at 0° C. under nitrogen, then trifluoroacetic acid (161 μL, 2.11 mmol) was added dropwise. The reaction mixture stirred at 0° C. for 20 minutes, then the ice bath was removed and the solution was allowed to warm to room temperature. The solution was stirred at room temperature overnight. The mixture was concentrated and purified by FCC, eluting with 0-70% EtOAc in heptane, to afford the title compound (2.76 g, 27%). δH (500 MHz, DMSO-d6) 7.38-7.32 (m, 4H), 7.30-7.23 (m, 1H), 4.13 (q, J 7.1 Hz, 2H), 3.75 (s, 2H), 3.60-3.51 (m, 4H), 2.05 (s, 3H), 1.22 (t, J 7.1 Hz, 3H).

Workup

  1. customthe ice bath was removed
  2. temperatureto warm to room temperature
  3. stirringThe solution was stirred at room temperature overnight
  4. concentrationThe mixture was concentrated
  5. custompurified by FCC
  6. washeluting with 0-70% EtOAc in heptane

Sources & evidence

ORD record
ord-04707362a582490c9ddbed181c4969e2
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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