Ethanol → HCID 12761157, compound

HRID 358272Notes

Reaction equation

HRID 358272 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)([CH3:13])[C:8]2=[O:12])=[CH:4][C:3]=1[O:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24].S(=O)(=O)(O)O.[CH2:31](O)[CH3:32]>>[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)([CH3:13])[C:8]2=[O:12])=[CH:4][C:3]=1[O:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:31][CH3:32])=[O:24]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric Acid2×HCID 12761158HCID 12761158, compound

Product 1

HCID 12761157HCID 12761157, compound

Procedure

To a suspension of 4-[(6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)-oxy]butanoic acid (0.5 g, 0.0012 mole) in absolute ethanol (50 ml) is added conc. sulfuric acid and the mixture is refluxed for 1 hr., treated with 3 Å molecular sieves and stirred at 25° for 18 hours. The reaction mixture is treated with more conc. sulfuric acid (0.2 ml) refluxed for 1 hr, filtered and treated with solid potassium carbonate. The ethanol is distilled at reduced pressure to give ethyl 4-[(6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)oxy]butanoate which is purified by chromatography on silica gel eluted with methylene chloride-tetrahydrofuran (100:1).

Workup

  1. temperaturethe mixture is refluxed for 1 hr
  2. addition, treated with 3 Å molecular sieves
  3. temperaturerefluxed for 1 hr
  4. filtrationfiltered
  5. additiontreated with solid potassium carbonate
  6. distillationThe ethanol is distilled at reduced pressure

Sources & evidence

ORD record
ord-2eec64e00d34401b905950a85f544170
Source dataset
uspto-grants-1984_08
Patent number
US04465850

Reaction notes

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