Water → HCID 13646823, compound

HRID 364808Notes

Reaction equation

HRID 364808 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[OH:19].C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].O>CN(C)C=O>[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][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 117544Ethyl 6-bromohexanoateHCID 123955886,7-Dichloro-2-cyclopentyl-5-hydroxy-2-methylindan-1-one

Product 1

HCID 13646823HCID 13646823, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6,7-Dichloro-2-cyclopentyl-2,3-dihydro-5-hydroxy-2-methyl-1H-inden-1-one (12 g., 0.04 mole) is dissolved in dimethylformamide (50 ml.), treated with potassium carbonate (5.5 g., 0.04 mole) and heated and stirred on a steam bath for 30 minutes. Ethyl 6-bromohexanoate (8.9 g., 0.04 mole) is added dropwise with good stirring over 15 minutes, then the mixture is heated and stirred in a steam bath for two hours. The reaction mixture is poured into water (400 ml.) and extracted with ether (2×150 ml.) The either extract is dried over sodium sulfate, filtered and the ether removed at reduced pressure. The residue, which crystallizes upon standing, is recrystallized from a mixture of ether and petroleum ether to give ethyl 6-[(6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)oxy]hexanoate, 16 g., m.p. 69°-72° C.

Workup

  1. temperatureheated
  2. stirringwith good stirring over 15 minutes
  3. temperaturethe mixture is heated
  4. stirringstirred in a steam bath for two hours
  5. extractionextracted with ether (2×150 ml.) The either
  6. extractionextract
  7. dry with materialis dried over sodium sulfate
  8. filtrationfiltered
  9. customthe ether removed at reduced pressure
  10. customThe residue, which crystallizes
  11. customis recrystallized from a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-15f6deee9f224fd6836afed41327e758
Source dataset
uspto-grants-1986_08
Patent number
US04605663

Reaction notes

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