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Hydrochloric Acid → Methyl {[2-(2-Acetoxyethyl)-6,7-dichloro-2,3-dihydro-1-oxo-1H-inden-5-yl]oxy}acetate

HRID 569300
Notes
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Reaction equation

HRID 569300 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH:7]1[CH2:15][C:14]2[C:9](=[C:10]([Cl:18])[C:11]([Cl:17])=[C:12]([OH:16])[CH:13]=2)[C:8]1=[O:19])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][C:28]([O:30][CH3:31])=[O:29].Cl>CN(C)C=O.O>[C:1]([O:4][CH2:5][CH2:6][CH:7]1[CH2:15][C:14]2[C:9](=[C:10]([Cl:18])[C:11]([Cl:17])=[C:12]([O:16][CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH:13]=2)[C:8]1=[O:19])(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 140981552-(Acetoxyethyl)-6,7-dichloro-2,3-dihydro-5-hydroxy-1H-inden-1-one

Product 1

HCID 14098156Methyl {[2-(2-Acetoxyethyl)-6,7-dichloro-2,3-dihydro-1-oxo-1H-inden-5-yl]oxy}acetateYield 96.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-(Acetoxyethyl)-6,7-dichloro-2,3-dihydro-5-hydroxy-1H-inden-1-one (5.8 gm, 0.0191 mole), potassium carbonate (3.97 gm, 0.0287 mole), methyl bromoacetate (3.52 gm, 0.023 mole) in dry N,N-dimethylformamide (35 ml) were stirred and heated at 60° C. for 3 hours. The mixture was cooled and poured into a mixture of water and ice containing hydrochloric acid. The resulting mixture was extracted with a mixture of ether and tetrahydrofuran then methylene chloride. The combined organic extracts were washed with water, then with brine and finally dried over MgSO4. Evaporation of the solvent gave 6.9 gm of residue which was purified by column chromatography using silica (300 gm) and eluting with a 50/1 mixture of methylene chloride and tetrahydrofuran. Combining the appropriate fractions and evaporating the solvent gave 3.3 gm of product, m.p. 111°-113° C.

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe resulting mixture was extracted with a mixture of ether and tetrahydrofuran
  3. washThe combined organic extracts were washed with water
  4. dry with materialwith brine and finally dried over MgSO4
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-7aaa239ebc3f4844824e6eaeac4ab07b
Source dataset
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04731471

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes