Cesium carbonate → HCID 86602541, compound

HRID 852378Notes

Reaction equation

HRID 852378 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH3:16])([CH3:7])[CH3:6])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].S(C1C=CC(C)=CC=1)(O[CH2:28][CH2:29][C:30]#[CH:31])(=O)=O>C(#N)C>[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:31][CH2:30][C:29]#[CH:28])=[CH:11][C:10]=1[CH3:16])([CH3:6])[CH3:7])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonate3×HCID 2720203-Butynyl p-toluenesulfonate3×HCID 16756990Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoate

Product 1

HCID 86602541HCID 86602541, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

2.38 g (10.00 mmol) 2-(4-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (described in WO 02/092590) and 1.63 g (5.00 mmol) Cs2CO3 were heated in 25 ml acetonitrile at reflux for 5 min. 2.34 (10.0 mmol) 3-Butynyl tosylate was added and heating was continued for 2.5 h. Then 1.63 g (5.00 mmol) Cs2CO3 and 2.34 (10.0 mmol) of 3-butynyl tosylate were added and the mixture was stirred at 60° C. (2.5 h). The temperature was raised to 95° C. and stirring continued for 12 h. Every 3 h 1.63 g (5.0 mmol) Cs2CO3 and 2.34 g (10.0 mmol) of 3-butynyl tosylate were added. The solvent was evaporated and the residue was redissolved in dichloromethane, dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (SiO2, n-heptane/EtOAc 2.5%) yielded 0.67 g of the title compound as light yellow oil.

Workup

  1. temperatureat reflux for 5 min
  2. temperatureheating
  3. temperatureThe temperature was raised to 95° C.
  4. stirringstirring
  5. waitcontinued for 12 h
  6. customThe solvent was evaporated
  7. dissolutionthe residue was redissolved in dichloromethane
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated
  11. customPurification by flash chromatography (SiO2, n-heptane/EtOAc 2.5%)

Sources & evidence

ORD record
ord-e691a4349efe4e039ec84b88abde2092
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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