Dimethylformamide → HCID 178488618, compound

HRID 1368549Notes

Reaction equation

HRID 1368549 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:11])[C:5]([O:9][CH3:10])=[C:6]([CH3:8])[CH:7]=1.[CH3:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([CH3:23])[C:20]=1[O:21]C)C=O.C([Li])C[CH2:26][CH3:27].C[N:30]([CH:32]=O)C.[Cl-].[NH4+:35]>C1COCC1.CCCCCC.C(OCC)(=O)C>[CH3:8][C:6]1[C:5]([O:9][CH3:10])=[C:4]([CH3:11])[CH:3]=[C:2]2[C:7]=1[CH:15]=[CH:18][C:19]([C:20]([C:26]1[N:35]=[CH:32][NH:30][CH:27]=1)([OH:21])[CH:13]([CH3:12])[CH3:14])=[CH:23]2

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 18520211HCID 18520211, compoundHCID 178418339Butyllithium

Product 1

HCID 178488618HCID 178488618, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

Production of 3,5-Dimethyl-4-methoxybenzaldehyde 5-Bromo-1,3-dimethyl-2-methoxybenzene (70.10 g) was dissolved in THF (700 ml). The solution was cooled to −78° C. To the reaction mixture was added dropwise n-butyl lithium in hexane (1.62 M, 250 ml), and the mixture was stirred for 15 min. To the mixture was added DMF (50 ml), and the temperature of the mixture was elevated to 0° C. To the reaction mixture was added an aqueous solution of ammonium chloride and ethyl acetate, and the mixture was extracted with ethyl acetate. The organic layer was dried and concentrated. To the residue was added ethyl acetate. The organic layer was washed with water and saturated solution of sodium chloride, dried and concentrated to give the titled compound (52.80 g) as an oil.

Workup

  1. customwas elevated to 0° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. additionTo the residue was added ethyl acetate
  6. washThe organic layer was washed with water and saturated solution of sodium chloride
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d2ee6e9a0be1441e8055d04740123814
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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