Ethyl diazoacetate → HCID 91324394, compound

HRID 1908670Notes

Reaction equation

HRID 1908670 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[CH2:6].[CH2:10]([O:12][C:13](=[O:17])[CH:14]=[N+]=[N-])[CH3:11]>C(Cl)Cl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[CH2:10]([O:12][C:13]([C@@H:14]1[CH2:6][C@H:5]1[C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[CH:3]=1)=[O:17])[CH3:11]

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 676913-Fluorostyrene

Product 1

HCID 91324394HCID 91324394, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 152122Dirhodium tetraacetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Around-bottomed flask was charged with 3-fluorostyrene (13.0 g, 0.107 mol) in anhydrous methylene chloride (130 mL). To this mixture was added rhodium acetate dimer (1.30 g, cat amount). A solution of ethyldiazoacetate (33.28 g, 0.291 mol) in anhydrous methylene chloride (130 mL) was added to the reaction via a syringe pump over 5 h and stirred at room temperature for 1 h in darkness. The reaction mixture was filtered through a plug of celite, which was washed with water followed by brine. The organic layer was dried over Na2SO4 and evaporated to dryness. Flash chromatography (silica, EtOAc/petroleum ether 1:9) gave rac-trans 2-(3-fluoro-phenyl)-cyclopropanecarboxylic acid ethyl ester (13.0 g, 59%) as a colorless liquid sufficiently pure for the next step.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of celite, which
  2. washwas washed with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-3658294eee614720b4f77f55f9772e90
Source dataset
uspto-grants-2013_12
Patent number
US08598213B2

Reaction notes

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