Water → HCID 178519272, compound

HRID 259588Notes

Reaction equation

HRID 259588 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([C-:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1)=O)=[O:5].[CH-:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.[Fe+2:26].S(=O)(=O)(O)O.O>C(O)(=O)C>[C-:12]1([C:10]2[CH2:9][CH2:8][CH2:7][C:6]=2[C:4](=[O:5])[C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=2[F:1])[CH:16]=[CH:15][CH:14]=[CH:13]1.[CH-:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.[Fe+2:26]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 178520609HCID 178520609, compound

Product 1

HCID 178519272HCID 178519272, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-(2-Fluorobenzoyl)-pentanoylferrocene (16g, 0.04 mole) and 5% v/v concentrated sulphuric acid in glacial acetic acid (300 ml) were stirred for 15 minutes at room temperature and were then poured into water. The aqueous layer was extracted with chloroform. The combined extracts were washed with water, dried (magnesium sulphate) and evaporated under vacuum. The resulting oil was purified by preparative thin layer chromatography using silica gel, with toluene as eluent, to yield pure b 1-ferrocenyl-2-[2-fluorobenzoyl)cyclopent-1-ene as red crystals; 1.2g (8%) mp 90°-92°.

Workup

  1. extractionThe aqueous layer was extracted with chloroform
  2. washThe combined extracts were washed with water
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated under vacuum
  5. customThe resulting oil was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-7b27081671cd47e786c61c8f0a901719
Source dataset
uspto-grants-1977_07
Patent number
US04038413

Reaction notes

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