Methanol → HCID 86745287, compound

HRID 1460707Notes

Reaction equation

HRID 1460707 reaction equation
[OH:1]OS([O-])=O.[K+].[C:7]1([C:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:15]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][S:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])[N:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CO>O.C(Cl)(Cl)Cl.C(OCC)(=O)C.CCCCCC>[OH2:1].[C:7]1([C:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:16]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:15]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][S:36]([CH2:37][C:38]([O:40][CH3:41])=[O:39])=[O:1])[N:14]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

8

Reactant 3

HCID 887MethanolHCID 15725742HCID 15725742, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 86745287HCID 86745287, compoundYield 141.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6212ChloroformSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-10 °C

Procedure

Oxone (potassium monopersulfate compound) (3.30 g, 5 mmol) was added in one portion to a stirred mixture of methyl [[6-(3,4,5-triphenyl-1H-pyrazol-1-yl)hexyl]thio]acetate (2.08 g, 4.3 mmol), methanol (100 mL) and water (50 mL) maintained at -10° C. The mixture was allowed to warm slowly to 0° C. and stirred for 45 minutes before being diluted with water and chloroform. The organic phase was separated and the aqueous layer extracted with CHCl3. The combined organic layers were washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo to give an oil. Chromatography on a column of silica gel using a mixture of ethyl acetate and hexane (7:3) as eluent furnished methyl [[6-(3,4,5-triphenyl-1H-pyrazol-1- yl)hexyl]sulfinyl]acetate hydrate (1.84 g, 85%) that slowly crystallized; m.p.=70.5°-71.5° C. MS(CI): m/e=501 (MH+).

Workup

  1. temperatureto warm slowly to 0° C.
  2. customThe organic phase was separated
  3. extractionthe aqueous layer extracted with CHCl3
  4. washThe combined organic layers were washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give an oil

Sources & evidence

ORD record
ord-d988eee382af44788d5c2c2ccff6acfe
Source dataset
uspto-grants-1991_12
Patent number
US05071866

Reaction notes

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