Ethyl ketone → HCID 13656859, compound

HRID 1788744Notes

Reaction equation

HRID 1788744 reaction equation
[CH3:1][N:2]([CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]#[CH:6].O1CCCC1.C([Li])CCC.[CH2:28]([C:30]([CH2:32][CH3:33])=[O:31])[CH3:29]>CCCCCC>[CH3:1][N:2]([CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]#[C:6][C:30]([CH2:32][CH3:33])([OH:31])[CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 7288Ethyl ketoneHCID 8028TetrahydrofuranHCID 13656858HCID 13656858, compoundHCID 178418339Butyllithium

Product 1

HCID 13656859HCID 13656859, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To 2 g N-methyl-N-(1-naphthylmethyl)-3-butyn-amine in abs. tetrahydrofurane (THF) are added dropwise, at -70°, 5.6 ml of a 15% by weight solution of n-butyllithium in hexane and half an hour later, at -70°, 0.95 ml diethylketone. The mixture is stirred for 3 hours at room temperature, poured onto ice and extracted with ether. The organic phase is washed, dried and evaporated in vacuum. The title compound (Compound 25) is obtained as an oil by chromatography over silica gel (with toluene/ethylacetate 3/1).

Workup

  1. customat -70°
  2. additionpoured onto ice
  3. extractionextracted with ether
  4. washThe organic phase is washed
  5. customdried
  6. customevaporated in vacuum

Sources & evidence

ORD record
ord-1d756b7823794bab81fbad4ad4cef0f6
Source dataset
uspto-grants-1987_08
Patent number
US04684661

Reaction notes

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