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

HRID 1873921Notes

Reaction equation

HRID 1873921 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-096e4794a3874da4a9be2ec9ae70f3e7
Source dataset
uspto-grants-2012_11
Patent number
US08304447B2

Reaction notes

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