Acetic Acid → 1-acetoxy-1-[(1-hydroxy)indan-5-yl]-2-[2-(N,N-dimethylamino)ethoxy]ethane

HRID 2257573Notes

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:22]C1CCCCO1)[CH2:17][CH2:16]2)[CH2:6][O:7][CH2:8][CH2:9][N:10]([CH3:12])[CH3:11])(=[O:3])[CH3:2].C(O)(=O)C.O1CCCC1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)C.O>[C:1]([O:4][CH:5]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[CH:18]([OH:22])[CH2:17][CH2:16]2)[CH2:6][O:7][CH2:8][CH2:9][N:10]([CH3:12])[CH3:11])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

1.8 g of 1-acetoxy-2-[2-(N,N-dimethylamino)ethoxy]-1-[1-(tetrahydropyran-2-yloxy)indan-5-yl]ethane was added to 30 ml of a 4:2:1 mixed solution of acetic acid, tetrahydrofuran and water. The resulting mixture was stirred at 70° C. for 2 hours. The reaction mixture was cooled and added to a mixture of 100 ml of water and 100 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/ethanol=10/1) to obtain 1.0 g of oily 1-acetoxy-1-[(1-hydroxy) indan-5-yl]-2-[2-(N,N-dimethylamino)ethoxy]ethane (compound No. 296).

Workup

temperatureThe reaction mixture was cooled
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/ethanol=10/1)

Sources & evidence

ORD record: ord-28da4b5422754766b3d60bc7e9ef8c25
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05658904

Reaction notes

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