tert-Butyl acrylate → 3-[2-(4-Hydroxy-phenyl)-morpholin-4-yl]-propionic acid tert-butyl ester

HRID 571792Notes

Reaction equation

HRID 571792 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH:3]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH2:2]1.[C:14]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:17])[CH:15]=[CH2:16]>CC#N>[C:19]([O:18][C:14](=[O:17])[CH2:15][CH2:16][N:1]1[CH2:6][CH2:5][O:4][CH:3]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH2:2]1)([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 15458tert-Butyl acrylateHCID 538045794-(Morpholin-2-yl)phenol

Product 1

HCID 666540623-[2-(4-Hydroxy-phenyl)-morpholin-4-yl]-propionic acid tert-butyl esterYield 77.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-morpholin-2-yl-phenol (3.95 g; 22.0 mmol), and tert-butyl acrylate (9.60 mL; 66.1 mmol) in CH3CN (100 mL) was heated under reflux overnight. After cooling to RT, the mixture was concentrated and purified by column chromatography (SiO2, Et2O) to afford 3-[2-(4-hydroxy-phenyl)-morpholin-4-yl]-propionic acid tert-butyl ester (5.22 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. concentrationthe mixture was concentrated
  4. custompurified by column chromatography (SiO2, Et2O)

Sources & evidence

ORD record
ord-2cc79abb9ad743c0a6bcad67135d317b
Source dataset
uspto-grants-2015_05
Patent number
US09029371B2

Reaction notes

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