Cesium carbonate → HCID 53948808, compound

HRID 363039Notes

Reaction equation

HRID 363039 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][CH2:13][CH3:14].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>CN(C=O)C>[CH:23]1([CH2:22][O:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[CH2:12][CH2:13][CH3:14])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 137636Cyclohexane, (bromomethyl)-HCID 11805593Methyl 4-hydroxy-3-propylbenzoate

Product 1

HCID 53948808HCID 53948808, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 22-4 (915 mg, 5.0 mmol) in 10 mL of DMF was added 1.78 g (5.50 mmol) of Cs2CO3 followed by 0.68 mL (4.9 mmol) of bromomethyl cyclohexane. The resulting solution was then heated at 50° C. for 24 h. The solvent was distilled under reduced pressure and the residue was taken up in 20 mL of EtOAc. The organic phase was extracted with 1N NaOH (2×50 mL), water (5×5 mL) and brine (5 mL), dried (MgSO4) and concentrated to afford 22-5 as an oil.

Workup

  1. distillationThe solvent was distilled under reduced pressure
  2. extractionThe organic phase was extracted with 1N NaOH (2×50 mL), water (5×5 mL) and brine (5 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0363a788c925406bba088720a04b4c65
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Reaction notes

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