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Water → 2-Oxopropyl [(5,6-Dichloro-9a-ethyl-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]acetate

HRID 223806
Notes
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Reaction equation

HRID 223806 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:20]([Cl:21])=[C:19]([O:22][CH2:23][C:24]([OH:26])=[O:25])[CH:18]=[C:17]2[C:9]=1[C:10]1[C:15]([CH2:27][CH3:28])([CH2:16]2)[CH2:14][CH2:13][C:12](=[O:29])[CH:11]=1.Cl[CH2:31][C:32](=[O:34])[CH3:33].O>CN(C)C=O.CCOCC>[Cl:7][C:8]1[C:20]([Cl:21])=[C:19]([O:22][CH2:23][C:24]([O:26][CH2:31][C:32](=[O:34])[CH3:33])=[O:25])[CH:18]=[C:17]2[C:9]=1[C:10]1[C:15]([CH2:27][CH3:28])([CH2:16]2)[CH2:14][CH2:13][C:12](=[O:29])[CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 12806939[(5,6-Dichloro-9a-ethyl-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]acetic acid

Product 1

HCID 128069492-Oxopropyl [(5,6-Dichloro-9a-ethyl-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]acetate

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (0.2 g) is suspended in a solution of [(5,6-dichloro-9a-ethyl-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]acetic acid (Example 20, Step D) (0.4 g, 0.0011 mole) in dimethylformamide (3 ml). After warming the suspension on a steam bath for 15 minutes, chloroacetone (0.5 g, 0.005 mole) is added and the mixture heated for an additional 15 minutes. The reaction mixture is cooled, poured into water (50 ml) and the product extracted into ether (three 15 ml portions. The extract is dried over Na2SO4. After filtration, the extract is concentrated to give a yellow oil. Trituration with cold ether causes crystallization to occur. The crystalline product weighs 0.1 g and melts at 153°-155° C.

Workup

  1. temperatureAfter warming the suspension on a steam bath for 15 minutes
  2. temperaturethe mixture heated for an additional 15 minutes
  3. temperatureThe reaction mixture is cooled
  4. extractionthe product extracted into ether (three 15 ml portions
  5. dry with materialThe extract is dried over Na2SO4
  6. filtrationAfter filtration
  7. concentrationthe extract is concentrated
  8. customto give a yellow oil
  9. customcrystallization

Sources & evidence

ORD record
ord-cda1f48f434d45fcaf4fa8d4e8a03d06
Source dataset
uspto-grants-1982_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04356313

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes