Dimethylformamide → HCID 22490925, compound

HRID 2180562Notes

Reaction equation

HRID 2180562 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[C:8]([CH3:16])([CH3:15])[CH2:7][CH:6]=[C:5]2[C:17]([CH3:20])([CH3:19])[CH3:18].C([Li])CCC.CN(C)[CH:28]=[O:29]>CCOCC>[C:17]([C:5]1[C:4]2[CH:3]=[C:2]([CH:28]=[O:29])[C:11]([O:12][CH2:13][CH3:14])=[CH:10][C:9]=2[C:8]([CH3:16])([CH3:15])[CH2:7][CH:6]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 22490955HCID 22490955, compoundHCID 178418339Butyllithium

Product 1

HCID 22490925HCID 22490925, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of 6-bromo-4-tert-butyl-7-ethoxy-1,1-dimethyl-1,2-dihydronaphthalene (Compound A-6, 600 mg, 1.78 mmol) in ether (10 mL) at −78° C. was added n-butyllithium (2.3 mL 1.6 M in hexane, 3.9 mmol). After stirring at −78° C. for 25 nm, N,N-dimethylformamide (2 mL) was added and the reaction mixture was allowed to warm to −40° C. over 10 min. The reaction mixture was quenched with water and extracted with ether. The combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 3% to 10% ethyl acetate in hexane) afforded the title compound as a white solid.

Workup

  1. additionwas added
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ether
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash column chromatography (silica gel, 3% to 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-0b73893715214586965a5837e3acd3fa
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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