Cyclopropyl methyl ketone → HCID 18950329, compound

HRID 1492390Notes

Reaction equation

HRID 1492390 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[C:6]([S:14][CH3:15])[C:5]=1[CH2:16][S:17][CH2:18][CH3:19].C1(C(C)=O)CC1>CO.O1CCCC1>[Cl:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[C:6]([S:14][CH3:15])[C:5]=1[CH2:16][S:17][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 13004Cyclopropyl methyl ketoneHCID 24758Sodium hydrideHCID 18950359HCID 18950359, compound

Product 1

HCID 18950329HCID 18950329, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Methanol (2 drops) was added to a mixture of sodium hydride (0.9 g) and tetrahydrofuran heated under reflux conditions. A mixture of methyl 4-chloro-3-ethylsulphenylmethyl-2-methylsulphenylbenzoate (4.0 g) and methyl cyclopropyl ketone (2.5 g) in tetrahydrofuran (36 ml) was added during 0.5 hours whilst maintaining at reflux. The mixture was stirred overnight at ambient temperature, and then quenched with methanol. Ether and water were added and the aqueous layer acidified (dilute hydrochloric acid), extracted (ether) and the ethereal solution extracted (sodium carbonate solution). This basic extract was re-acidified (hydrochloric acid), extracted (ether) and evaporated to give 4-chloro-3-ethylsulphenylmethyl-2-methylsulphenylbenzoic acid (3.0 g), NMR (CDCl3) 1.35 (t,3H), 2.5 (s,3H), 2.7 (q,2H), 4.3 (s,2H), 7.5 (d,1H), 7.8 (d,1H).

Workup

  1. temperatureheated under reflux conditions
  2. additionwas added during 0.5 hours
  3. temperaturewhilst maintaining
  4. temperatureat reflux
  5. customquenched with methanol
  6. additionEther and water were added
  7. extractionextracted (ether)
  8. extractionthe ethereal solution extracted (sodium carbonate solution)
  9. extractionThis basic extract
  10. extractionextracted (ether)
  11. customevaporated

Sources & evidence

ORD record
ord-3cee480c4b8941748bf14e36ffe38e64
Source dataset
uspto-grants-1994_12
Patent number
US05374606

Reaction notes

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