Cesium carbonate → HCID 23159322, compound

HRID 1295091Notes

Reaction equation

HRID 1295091 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:11])[C:9]=1[OH:10])[CH:5]=[O:6].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:18]([O:20][C:21](=[O:26])[C:22](Br)([CH3:24])[CH3:23])[CH3:19]>CC(C)C(=O)C>[CH2:18]([O:20][C:21](=[O:26])[C:22]([O:10][C:9]1[C:8]([CH3:11])=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[CH3:1])([CH3:24])[CH3:23])[CH3:19]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 752223,5-Dimethyl-4-hydroxybenzaldehyde

Product 1

HCID 23159322HCID 23159322, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 112513-Methyl-2-butanoneSolvent

Procedure

A solution of 3,5-Dimethyl-4-hydroxybenzaldehyde (20 g, 0.133 mol) in 3-Methyl-2-butanone (400 mL) was treated with Cs2CO3 (86.9 g, 2 eq.) and Ethyl-2-bromoisobutyrate (39.2 L, 2 eq.). The resulting mixture was stirred at reflux for 36 hours. After cooling to rt the reaction mixture was filtered off. The cake was washed with ethyl acetate. The filtrate was evaporated off and the residue was diluted with ethyl acetate (1 L), washed with water (500 mL) and then with NaOH 1N (500 mL). The organic layer was drying over Na2SO4 and filtration evaporation gave the title compound (31.8 g, 0.12 mol) as a brown oil in a 90% yield.

Workup

  1. temperatureat reflux for 36 hours
  2. filtrationwas filtered off
  3. washThe cake was washed with ethyl acetate
  4. customThe filtrate was evaporated off
  5. additionthe residue was diluted with ethyl acetate (1 L)
  6. washwashed with water (500 mL)
  7. dry with materialThe organic layer was drying over Na2SO4 and filtration evaporation

Sources & evidence

ORD record
ord-82b76abc90584f3aa4f8a79468151253
Source dataset
uspto-grants-2007_07
Patent number
US07241793B2

Reaction notes

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