Diethylamine → (e)-Methyl 2-[[2-[3-(diethylamino)-1-oxo-2-propenyl]-5-methoxyphenoxy]methyl]benzoate

HRID 1265162Notes

Reaction equation

HRID 1265162 reaction equation
O/[CH:2]=[CH:3]/[C:4]([C:6]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:7]=1[O:8][CH2:9][C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])=[O:5].[CH2:26]([NH:28][CH2:29][CH3:30])[CH3:27]>C1(C)C=CC=CC=1>[CH2:26]([N:28]([CH2:29][CH3:30])/[CH:2]=[CH:3]/[C:4]([C:6]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:7]=1[O:8][CH2:9][C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])=[O:5])[CH3:27]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 11727588(e)-Methyl 2-[[2-(3-hydroxy-1-oxo-2-propenyl)-5-methoxyphenoxy]methyl]benzoate

Product 1

HCID 11058397(e)-Methyl 2-[[2-[3-(diethylamino)-1-oxo-2-propenyl]-5-methoxyphenoxy]methyl]benzoateYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 2 L round bottomed flask was added (E)-methyl 2-[[2-(3-hydroxy-1-oxo-2-propenyl)-5-methoxyphenoxy]methyl]benzoate (104 g, 0.304 mol) and 1 L of toluene. After complete dissolution, diethylamine (28.3g, 40 mL, 0.39 mol) was rapidly added under nitrogen via an addition funnel into the stirred solution. The reaction mixture was stirred under nitrogen for 1 h and it was then concentrated under reduced pressure to give approximately 120 g (100% yield) of the title compound as an orange solid: 1H NMR (300 MHz, CDCl3) δ 8.02 (1H, d), 7.84 (1H, d), 7.67 (2H, bd), 7.51 (1H, t) 7.35 (1H, t), 6.54 (2H, m), 5.75 (1H, d), 5.52 (2H, s), 3.80 (3H, s), 3.23 (4h, br), 1.14 (6H, br).

Workup

  1. additionwas rapidly added under nitrogen via an addition funnel into the stirred solution
  2. concentrationit was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-2ee54fc75d7d4e12bb7c9f08f8d4ebc5
Source dataset
uspto-grants-2003_04
Patent number
US06545031B1

Reaction notes

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