Water → HCID 57014598, compound

HRID 1680971Notes

Reaction equation

HRID 1680971 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([F:23])[C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH:11]2[OH:14])=[CH:7][CH:6]=1.[N+](=[CH:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N-].O>C1(C)C=CC=CC=1.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[Cl:1][C:2]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([F:23])[C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH:11]2[O:14][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 12192Ethyl diazoacetateHCID 19807756HCID 19807756, compound

Product 1

HCID 57014598HCID 57014598, compound

Reagents, catalysts & solvents 2

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 1140TolueneSolvent2×

Procedure

Rhodium (II) acetate dimer (approximately 10mg) was suspended in a solution of the indanol (Example 3, step B, 0.5g) in dry toluene (10 cm3). A solution of ethyl diazoacetate (0.18g) in a small volume of dry toluene was slowly added dropwise to the reaction mixture. Effervescence was observed, the solid dissolved and the solution turned a blue green colour. The mixture was allowed to stand at room temperature overnight then poured into water. The aqueous mixture was extracted with diethyl ether, washed with brine, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. Preparative thin layer chromatography (silica/hexane-ether, 7:3) gave compound 3, ethyl (RS)-6-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)indan-1-yloxyacetate, as a colourless oil (0.17g,27%).

Workup

  1. dissolutionthe solid dissolved
  2. extractionThe aqueous mixture was extracted with diethyl ether
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2d23d5a974ea4822948a4d599ead8e14
Source dataset
uspto-grants-1992_12
Patent number
US05167696

Reaction notes

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