Dimethylformamide → 2-(Dimethylamino)-3-methylbenzaldehyde

HRID 215930Notes

Reaction equation

HRID 215930 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[N:4]([CH3:6])[CH3:5].[Li]C(C)(C)C.CCCCC.CN([CH:25]=[O:26])C>CCOCC>[CH3:5][N:4]([CH3:6])[C:3]1[C:7]([CH3:11])=[CH:8][CH:9]=[CH:10][C:2]=1[CH:25]=[O:26]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8003PentaneHCID 58006241HCID 58006241, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 130217582-(Dimethylamino)-3-methylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Compound 150 (0.17 g, 0.81 mmol) in Et2O (5.0 mL) at −78° C. under Argon atmosphere was added dropwise a solution of 1.7M t-BuLi in pentane (1.0 mL, 1.79 mmol), and the reaction was stirred for 1 h. DMF (0.25 mL, 3.24 mmol) was added, and the cooling bath was removed. After 1h15, the reaction was cooled to 0° C., and saturated NH4Cl was added. The mixture was extracted with EtOAc, washed with brine, dried over MgSO4, and filtered. The solvent was removed, and the residue was purified by silica gel flash chromatography with EtOAc (15%) and hexanes (85%) as eluent to produce Compound 151 as a yellow oil.

Workup

  1. customthe cooling bath was removed
  2. additionsaturated NH4Cl was added
  3. extractionThe mixture was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed
  8. customthe residue was purified by silica gel flash chromatography with EtOAc (15%) and hexanes (85%) as eluent

Sources & evidence

ORD record
ord-e9def0dcc01c49aeb9e729b45933fda2
Source dataset
uspto-grants-2012_06
Patent number
US08193203B2

Reaction notes

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