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

HRID 1402680Notes

Reaction equation

HRID 1402680 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-91570014f3394479b32a6526812ad449
Source dataset
uspto-grants-2014_12
Patent number
US08912177B2

Reaction notes

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