Cesium carbonate → 2,6-Dimethyl-4-(2-oxo-2-pyrrolidin-1-yl-ethoxy)-benzaldehyde

HRID 1514878Notes

Reaction equation

HRID 1514878 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([CH:6]=[O:7])=[C:4]([CH3:11])[CH:3]=1.Cl[CH2:13][C:14]([N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:15].C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[CH3:11][C:4]1[CH:3]=[C:2]([O:1][CH2:13][C:14](=[O:15])[N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:9]=[C:8]([CH3:10])[C:5]=1[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 884401-(Chloroacetyl)pyrrolidineHCID 5910722,6-Dimethyl-4-hydroxybenzaldehyde

Product 1

HCID 866512572,6-Dimethyl-4-(2-oxo-2-pyrrolidin-1-yl-ethoxy)-benzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-hydroxy-2,6-dimethyl-benzaldehyde (87 mg), 2-chloro-1-pyrrolidin-1-yl-ethanone (102 mg), and Cs2CO3 (375 mg, 1.15 mmol) in acetone (4 mL) was stirred at room temperature for 16 h. The mixture was concentrated, diluted with water, and extracted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to give 2,6-dimethyl-4-(2-oxo-2-pyrrolidin-1-yl-ethoxy)-benzaldehyde: MS (m/z) 262 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f6a7b1e16949452eb137c371c4c77f2e
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

Loading…