Hexane → HCID 19783086, compound

HRID 257338Notes

Reaction equation

HRID 257338 reaction equation
[F:1][C:2]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1.CCCCCC>C1(C)C=CC=CC=1>[F:1][C:2]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:7][CH2:6][CH2:5][CH:4]=[C:3]1[SH:23]

Participants

5

Reactant 3

HCID 8058HexaneHCID 87949Lawesson's reagentHCID 10921276Ethyl 1-fluoro-2-oxocyclohexanecarboxylate

Product 1

HCID 19783086HCID 19783086, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Referring to the process described in Bulletin des Societe Chimiques Belges volume 87, page 223 (1978), 5.4 g (30 mmol) of ethyl 1-fluoro-2-oxocyclohexanecarboxylate was dissolved in 50 ml of toluene, to this was added 6.0 g (15 mmol) of Lawesson's reagent, and reaction was carried out at 100° C. for 5 hours. 100 ml of hexane was added, the precipitate was filtered out and the solvent was distilled away. The filtrate was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate=15/1) to obtain 1.1 g (yield: 18 % of ethyl 1-fluoro-2-mercapto-2-cyclohexenecarboxylate.

Workup

  1. additionto this was added
  2. filtrationthe precipitate was filtered out
  3. distillationthe solvent was distilled away
  4. customThe filtrate was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate=15/1)

Sources & evidence

ORD record
ord-b4997bd2b13145f382fa1fd4454cd9c4
Source dataset
uspto-grants-1993_11
Patent number
US05262385

Reaction notes

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