Methyl Acrylate → HCID 69697317, compound

HRID 897224Notes

Reaction equation

HRID 897224 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C@@H:11]([NH2:13])[CH3:12].[C:14]([O:18][CH3:19])(=[O:17])[CH:15]=[CH2:16]>C(O)(=O)C>[CH3:19][O:18][C:14](=[O:17])[CH2:15][CH2:16][N:13]([CH2:16][CH2:15][C:14]([O:18][CH3:19])=[O:17])[C@H:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[CH3:12]

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 1201503(1S)-1-(Naphthalen-2-yl)ethan-1-amine

Product 1

HCID 69697317HCID 69697317, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(S)-(−)-1-(2-Naphthyl)ethylamine (2.28 g, 13 mmol) was added dropwise to a solution of methyl acrylate (5 mL, 55 mmol) and acetic acid (0.26 mL) with stirring in a sealed tube. A white crystalline solid precipitated out of solution. The temperature was then elevated to 80° C., at which time a clear solution was formed again. Stirring was continued for 18 hours. Excess methyl acrylate and acetic acid were removed under reduced pressure. The crude oil was purified by chromatography on silica gel with ethyl acetate/hexanes (1:4) to give the title compound (3.6 g, 77%) as a pale yellow oil. 1H NMR (300 MHz, CDCl3) δ 1.45 (3H, d, J=6.78 Hz), 2.45 (4H, t, J=7.35 Hz), 2.73-2.94 (4H, m), 3.62 (6H, s), 4.00 (1H, q, J=6.78 Hz), 7.41-7.53 (3H, m), 7.70-7.84 (4H, m).

Workup

  1. customA white crystalline solid precipitated out of solution
  2. customwas then elevated to 80° C., at which time
  3. customwas formed again
  4. stirringStirring
  5. customExcess methyl acrylate and acetic acid were removed under reduced pressure
  6. customThe crude oil was purified by chromatography on silica gel with ethyl acetate/hexanes (1:4)

Sources & evidence

ORD record
ord-79f1de8538c543cb9ea2b8b8782f0075
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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