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Pyridine → 1-acetoxy-2-[2-(N,N-dimethylamino)ethoxy]-1-[1-(tetrahydropyran-2-yloxy)indan-5-yl]ethane

HRID 2257572
Notes
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Reaction equation

HRID 2257572 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][O:6][CH2:7][CH:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[CH:15]([O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1)[CH2:14][CH2:13]2)[OH:9])[CH3:3].[C:26](OC(=O)C)(=[O:28])[CH3:27].N1C=CC=CC=1>C(OCC)C>[C:26]([O:9][CH:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[CH:15]([O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1)[CH2:14][CH2:13]2)[CH2:7][O:6][CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])(=[O:28])[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 542682892-[2-(N,N-dimethylamino)ethoxy]-1-[1-(tetrahydropyran-2-yloxy)indan-5-yl]ethanol

Product 1

HCID 538846171-acetoxy-2-[2-(N,N-dimethylamino)ethoxy]-1-[1-(tetrahydropyran-2-yloxy)indan-5-yl]ethane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2.5 g of 2-[2-(N,N-dimethylamino)ethoxy]-1-[1-(tetrahydropyran-2-yloxy)indan-5-yl]ethanol, 8 ml of acetic anhydride and 0.64 ml of pyridine was stirred at room temperature for 1 hour. The reaction mixture was added to a mixture of 50 ml of ice water and 50 ml of diethyl ether. 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 1.9 g of oily 1-acetoxy-2-[2-(N,N-dimethylamino)ethoxy]-1-[1-(tetrahydropyran-2-yloxy)indan-5-yl]ethane (compound No. 295).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation under reduced pressure
  4. customThe residue thus obtained
  5. customwas purified by column chromatography (eluant:chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-9296c69dbe854df99427122bad00602f
Source dataset
uspto-grants-1997_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05658904

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes