Cesium carbonate → HCID 18779729, compound

HRID 1421752Notes

Reaction equation

HRID 1421752 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-3f26f991f27849689da04f91ccbdc56c
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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