Chloroform → HCID 53703941, compound

HRID 1701166Notes

Reaction equation

HRID 1701166 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([S:16]([CH2:18][C:19]([OH:21])=[O:20])=[O:17])[CH3:15])=[CH:10][CH:9]=1.[OH-].[K+].[CH:24](Cl)(Cl)Cl.CI>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:24][O:20][C:19](=[O:21])[CH2:18][S:16]([CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[CH:9][CH:10]=1)[CH3:15])=[O:17]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 20348737HCID 20348737, compound

Product 1

HCID 53703941HCID 53703941, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Procedure

1.1 gm (3 millimols) of tetrabutylammonium iodide and 3.06 gm (10 millimols) of [1-(2'-fluoro-4-biphenylyl)-ethylsulfinyl]-acetic acid (m.p. 164°-165° C.) were added to a solution of 730 mgm (13 millimols) of potassium hydroxide in 20 ml of water, then 20 ml of chloroform and 2 ml of methyl iodide were added, and the mixture was stirred at room temperature for 10 hours. Afterwards, the organic phase was separated from the neutral aqueous phase, washed with dilute hydrochloric acid and then with water, dried and evaporated. The residue (3.6 gm) was purified by chromatography on 100 gm of silicagel (grain size: 0.05-0.2 mm) with cyclohexane ethyl acetate=1/4. After evaporation of the combined fractions with an Rf -value of 0.4 and recrystallization of the residue from isopropanol, 1.7 gm (53% of theory) of the title compound m.p. 75°-77° C. were obtained.

Workup

  1. customAfterwards, the organic phase was separated from the neutral aqueous phase
  2. washwashed with dilute hydrochloric acid
  3. dry with materialwith water, dried
  4. customevaporated
  5. customThe residue (3.6 gm) was purified by chromatography on 100 gm of silicagel (grain size: 0.05-0.2 mm) with cyclohexane ethyl acetate=1/4
  6. customAfter evaporation of the combined fractions
  7. customwith an Rf -value of 0.4 and recrystallization of the residue from isopropanol, 1.7 gm (53% of theory) of the title compound m.p. 75°-77° C.
  8. customwere obtained

Sources & evidence

ORD record
ord-5b279a8695ed460f8018d6edb9b30545
Source dataset
uspto-grants-1980_03
Patent number
US04191776

Reaction notes

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