Dimethylformamide → 2,3-Dimethoxynaphthalene-1-carbaldehyde

HRID 1070673Notes

Reaction equation

HRID 1070673 reaction equation
C([Li])CCC.[CH3:6][O:7][C:8]1[C:17]([O:18][CH3:19])=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1.CN(C)CCN(C)C.CN([CH:31]=[O:32])C>CCCCCC.CCOCC>[CH3:19][O:18][C:17]1[C:8]([O:7][CH3:6])=[CH:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]=1[CH:31]=[O:32]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 6047082,3-DimethoxynaphthaleneHCID 178418339Butyllithium

Product 1

HCID 134305632,3-Dimethoxynaphthalene-1-carbaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

n-Butyl lithium in hexane (1.6 N, 31.3 ml) was gradually added to a solution of 2,3-dimethoxynaphthalene (9.4 g) and N,N,N′,N′-tetramethylethylenediamine (7.4 ml) in ether (150 ml) under argon at 0° C. The reaction mixture was stirred at room temperature for two hours, cooled to 0° C. and DMF (7.3 g) in ether (20 ml) added. The reaction mixture was stirred at room temperature overnight and poured in ice water. The product was extracted with ether, washed with water, dried, evaporated and recrystallized from ether. Yield: 4.2 g.

Workup

  1. temperaturecooled to 0° C.
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. extractionThe product was extracted with ether
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customrecrystallized from ether

Sources & evidence

ORD record
ord-5bc8112158354fdc8017dabae43407c3
Source dataset
uspto-grants-2005_06
Patent number
US06903114B2

Reaction notes

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