Cesium carbonate → HCID 18779729, compound

HRID 1585924Notes

Reaction equation

HRID 1585924 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([OH:16])[CH:9]=1)(C)(C)C.[C:19]1([CH2:25][CH2:26][CH2:27]Br)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[OH:6][CH2:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([O:16][CH2:27][CH2:26][CH2:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 12503(3-Bromopropyl)benzeneHCID 131721347HCID 131721347, compound

Product 1

HCID 18779729HCID 18779729, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-benzonitrile from step 2 (50 mg, 0.19 mmol) was dissolved in DMF (1 ml) and treated with phenylpropylbromide (29 μl, 0.19 mmol). Cs2CO3 (68 mg, 0.21 mmol) was then added and the reaction mixture stirred at room temp. for 14 hours. The mixture was filtered and washed with DMF (3×10 mL). The solvent was removed in vacuo and the residue was purified by flash chromatography (10% EtOAc/Hexane) to yield desired product.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with DMF (3×10 mL)
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by flash chromatography (10% EtOAc/Hexane)

Sources & evidence

ORD record
ord-0543e73733044b7eadb8e9b04bf35e73
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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