tert-Butyl acrylate → HCID 67032480, compound

HRID 920564Notes

Reaction equation

HRID 920564 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:14])[CH:5]=[CH:6][C:7]=1[CH:8]1[O:13][CH2:12][CH2:11][NH:10][CH2:9]1.[C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])[CH:16]=[CH2:17]>CC#N>[C:20]([O:19][C:15](=[O:18])[CH2:16][CH2:17][N:10]1[CH2:11][CH2:12][O:13][CH:8]([C:7]2[CH:6]=[CH:5][C:4]([OH:14])=[CH:3][C:2]=2[CH3:1])[CH2:9]1)([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 15458tert-Butyl acrylateHCID 67032452HCID 67032452, compound

Product 1

HCID 67032480HCID 67032480, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-methyl-4-morpholin-2-yl-phenol (14.26 g; 73.8 mmol) and tert-butyl acrylate (21.4 ml; 147.6 mmol) in CH3CN (250 mL) was heated under reflux overnight. After cooling to RT the mixture was concentrated in vacuo, and the residue was partitioned between EtOAc and 5% aqueous NaHCO3 solution. The organic layer was dried (Na2SO4), filtered, concentrated in vacuo, and purified by column chromatography (SiO2, CH2Cl2>Et2O/hexanes 1:1>Ether) to afford 3-[2-(4-hydroxy-2-methyl-phenyl)-morpholin-4-yl]-propionic acid tert-butyl ester (22.62 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. concentrationwas concentrated in vacuo
  4. customthe residue was partitioned between EtOAc and 5% aqueous NaHCO3 solution
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified by column chromatography (SiO2, CH2Cl2>Et2O/hexanes 1:1>Ether)

Sources & evidence

ORD record
ord-0dc6fa2342f1493a95e720319851822a
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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