Dimethylformamide → HCID 19967148, compound

HRID 976343Notes

Reaction equation

HRID 976343 reaction equation
C([Li])CCC.[CH3:6][O:7][CH2:8][O:9][C:10]1[CH:19]=[CH:18][C:17]2[C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][C:13]([CH3:23])([CH3:22])[C:12]=2[CH:11]=1.CN(C)[CH:26]=[O:27].[Cl-].[NH4+]>CCCCCC.C(OCC)C>[CH:26]([C:19]1[C:10]([O:9][CH2:8][O:7][CH3:6])=[CH:11][C:12]2[C:13]([CH3:23])([CH3:22])[CH2:14][CH2:15][C:16]([CH3:21])([CH3:20])[C:17]=2[CH:18]=1)=[O:27]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 22347859HCID 22347859, compoundHCID 178418339Butyllithium

Product 1

HCID 19967148HCID 19967148, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

22 ml of a 1.56M solution of n-butyllithium in hexane was dropwise added to 40 ml of a solution of 5.7 g of 5,6,7,8-tetrahydro-2-methoxymethoxy-5,5,8,8-tetramethylnaphthalene in anhydrous diethyl ether at -78° C. The temperature of the mixture was gradually raised to room temperature (in 10 minutes). The resulting mixture was stirred for 5 hours and cooled to -78° C., followed by the dropwise addition thereto of 5 ml of a solution of 2.6 g of N,N-dimethylformamide in diethyl ether. The temperature of the obtained mixture was gradually raised to room temperature (in 10 minutes). The resulting mixture was stirred for 3 hours, followed by the addition thereto of 30 ml of a saturated aqueous solution of ammonium chloride. The obtained mixture was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified by silica gel chromatography (developer: 10% ethyl acetate/n-hexane) to give 4.2 g of the title compound as a white solid.

Workup

  1. temperaturecooled to -78° C.
  2. additionfollowed by the dropwise addition
  3. temperatureThe temperature of the obtained mixture was gradually raised to room temperature (in 10 minutes)
  4. stirringThe resulting mixture was stirred for 3 hours
  5. additionfollowed by the addition
  6. extractionThe obtained mixture was extracted with ethyl acetate
  7. washThe organic phase was washed with a saturated aqueous solution of common salt
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationdistilled
  10. customto remove the solvent
  11. customThe residue was purified by silica gel chromatography (developer: 10% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-8b1f8d83195f46678961fa5aeec2d94e
Source dataset
uspto-grants-1997_03
Patent number
US05612356

Reaction notes

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