4-Methylmorpholine → (Z)-tert-butyl 3-(4-(2-methoxyethyl)phenoxy)acrylate

HRID 919020

Reaction equation

HRID 919020 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[C:12]([O:16][C:17](=[O:20])[C:18]#[CH:19])([CH3:15])([CH3:14])[CH3:13].CN1CCOCC1>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11]/[CH:19]=[CH:18]\[C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:20])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 925164-(2-Methoxyethyl)phenolHCID 543038tert-Butyl propiolate

Product 1

HCID 67168776(Z)-tert-butyl 3-(4-(2-methoxyethyl)phenoxy)acrylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

a mixture of 4-(2-methoxy ethyl)phenol (1.547 g, 10.3 mmol), propiolic acid tert-butyl ester (1.367 g, 10.8 mmol) and N-methyl morpholine (1.18 mL, 10.8 mmol) in CH2Cl2 (15 mL) was stirred at room temperature for 24 hours. The mixture was absorbed on SiO2 (20 g) and purified by column chromatography using a mixture of methylene chloride/hexane. The product was obtained as a two to one mixture of (E)/(Z)-tert-butyl 3-(4-(2-methoxyethyl)phenoxy)acrylate isomers (2.0 g).

Workup

  1. customThe mixture was absorbed on SiO2 (20 g)
  2. custompurified by column chromatography
  3. additiona mixture of methylene chloride/hexane

Sources & evidence

ORD record
ord-27fe801f7c40487d879d71328d0bfc47
Source dataset
uspto-grants-2016_03
Patent number
US09272996B2

Linked notes

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