Dimethylformamide → HCID 86635911, compound

HRID 561788Notes

Reaction equation

HRID 561788 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:17])=[C:6]([CH:16]=1)[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].C([Li])CCC.CN([CH:26]=[O:27])C>C1COCC1>[Si:9]([O:8][CH2:7][C:6]1[CH:16]=[C:2]([CH:3]=[CH:4][C:5]=1[Cl:17])[CH:26]=[O:27])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 58007486HCID 58007486, compoundHCID 178418339Butyllithium

Product 1

HCID 86635911HCID 86635911, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [(5-bromo-2-chlorobenzyl)oxy](tert-butyl)dimethylsilane from the previous step (1 eq.) in THF (0.08 M) was added, at −78° C., n-butyl lithium (2.5 M hexane solution, 1.1 eq) dropwise over 15 min. The reaction mixture was stirred at −78° C. for a further 30 min before DMF (2 eq.) was slowly added. The resulting solution was allowed to warm to RT over 3 h and then quenched with H2O. The organic layer was separated and the aqueous layer was back-extracted with EtOAc. The combined organic extracts were washed with sat. aq. NaHCO3 and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded an orange oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc) afforded the title compound as a yellow oil.

Workup

  1. additionwas slowly added
  2. customquenched with H2O
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was back-extracted with EtOAc
  5. washThe combined organic extracts were washed with sat. aq. NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customConcentration of the filtrate in vacuo afforded an orange oil
  9. customPurification of the crude product
  10. customthus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-d1c8dbfbf4f040938504d8aecf8e01cb
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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