N,N,N',N'-Tetramethylethylenediamine → HCID 23035563, compound

HRID 1710150Notes

Reaction equation

HRID 1710150 reaction equation
C([Li])CCC.[C:6]1([S:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:24]([O:27][CH3:28])[O:25][CH3:26])=[CH:16]2)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CN(C)CCN(C)C.[CH3:37][O:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][C:46]=1[O:47][CH3:48])[CH:42]=[O:43]>CCCCCC.O1CCCC1.O>[C:6]1([S:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:24]([O:25][CH3:26])[O:27][CH3:28])=[C:16]2[CH:42]([OH:43])[C:41]2[CH:44]=[CH:45][C:46]([O:47][CH3:48])=[C:39]([O:38][CH3:37])[CH:40]=2)(=[O:13])=[O:14])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8419VeratraldehydeHCID 10336805HCID 10336805, compoundHCID 178418339Butyllithium

Product 1

HCID 23035563HCID 23035563, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

40 ml of 1.55M n-butyl lithium in hexane are added under stirring with cooling to a tetrahydrofuran solution of 19 g of 1-phenylsulfonyl-3-dimethoxymethylindole and 6.5 g of N,N,N',N'-tetramethylethylenediamine. The mixture is stirred at room temperature, and then a solution of 9.3 g of 3,4-dimethoxybenzaldehyde in tetrahydrofuran is added thereto under cooling. The mixture is further stirred at room temperature, poured into water, and then extracted with ethyl acetate. The extract is dried and evaporated under reduced pressure to remove the solvent. The residue is purified by using silica gel column. 17 g of 1-phenylsulfonyl-2-(α-hydroxy-3,4-dimethoxybenzyl)-3-dimethoxymethylindole are obtained as syrup.

Workup

  1. stirringThe mixture is stirred at room temperature
  2. temperatureunder cooling
  3. stirringThe mixture is further stirred at room temperature
  4. extractionextracted with ethyl acetate
  5. customThe extract is dried
  6. customevaporated under reduced pressure
  7. customto remove the solvent
  8. customThe residue is purified

Sources & evidence

ORD record
ord-4ee1cec873354c47aecb283737db203f
Source dataset
uspto-grants-1990_08
Patent number
US04952602

Reaction notes

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