Dimethylformamide → HCID 21706869, compound

HRID 1594947Notes

Reaction equation

HRID 1594947 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:6]=[CH:5]2.C([Li])CCC.CN([CH:25]=[O:26])C>C1COCC1>[C:13]([O:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH:25]=[O:26])[CH:3]=2)[CH:8]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 21707225HCID 21707225, compoundHCID 178418339Butyllithium

Product 1

HCID 21706869HCID 21706869, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a −78° C. solution of 6-bromo-2-t-butyloxynaphthalene (2.00 g, 7.16 mmol) in dry THF (30 mL) under nitrogen was added 2.5 m n-butyl lithium in hexanes (3.16 mL, 7.88 mmol). The resulting solution was stirred 0.5 hours at −78° C. and dry DMF (1.66 mL, 21.56 mL) was added neat. The cooling bath was removed, the reaction was allowed to stir for 1 h, and quenched with excess saturated ammonium chloride. The reaction was partitioned between ethyl acetate and brine. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated under vacuum. Purification on silica gel with 10% ethyl acetate/hexanes gave the title compound (1.47 g, 90%) as a colorless oil. mp 51-52° C.;

Workup

  1. customThe cooling bath was removed
  2. stirringto stir for 1 h
  3. customquenched with excess saturated ammonium chloride
  4. customThe reaction was partitioned between ethyl acetate and brine
  5. washThe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customPurification on silica gel with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-4ec3af302aaf4fbabbd92a60ecb91dab
Source dataset
uspto-grants-2001_09
Patent number
US06284796B1

Reaction notes

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