Diethyl Ether → 1-acetoxy-1-(1H-inden-6-yl)-2-[2-(N,N-dimethylamino)ethoxy]ethane
Reaction equation
[C:1]([O:4][CH:5]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[CH:18](O)[CH2:17][CH2:16]2)[CH2:6][O:7][CH2:8][CH2:9][N:10]([CH3:12])[CH3:11])(=[O:3])[CH3:2].CS(Cl)(=O)=O.C(OCC)C.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1>[C:1]([O:4][CH:5]([C:13]1[CH:14]=[C:15]2[C:19]([CH:18]=[CH:17][CH2:16]2)=[CH:20][CH:21]=1)[CH2:6][O:7][CH2:8][CH2:9][N:10]([CH3:12])[CH3:11])(=[O:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
In 5 ml of pyridine was dissolved 1.0 g of 1-acetoxy-1-[(1-hydroxy)indan-5-yl]-2-[2-(N,N-dimethylamino)-ethoxy]ethane. To the solution was added 0.3 ml of methanesulfonyl chloride at room temeprature. The resulting mixture was stirred at the same temperature overnight. The reaction mixture was added to a mixture of 50 ml of ice water and 50 ml of diethyl ether. The resulting mixture was adjusted to pH 8.5 with potassium carbonate. The organic layer was separated and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography (eluant: chloroform/methanol=10/1) to obtain 80 mg of oily 1-acetoxy-1-(1H-inden-6-yl)-2-[2-(N,N-dimethylamino)ethoxy]ethane (compound No. 297).
Workup
- customThe organic layer was separated
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was removed by distillation under reduced pressure
- customThe residue thus obtained
- customwas purified by column chromatography (eluant: chloroform/methanol=10/1)
Sources & evidence
- ORD record
- ord-578e02170d2547619c681da33241904c
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05719150
Reaction notes
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