Water → 4-(Methanesulfinyl)benzaldehyde

HRID 1760764Notes

Reaction equation

HRID 1760764 reaction equation
ClC[CH2:3][S:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2C(C3C=CC(O)=CC=3)=C(C(F)(F)F)C3C=CC(O)=CC=3[O:12]2)=[CH:7][CH:6]=1.[I-].[K+].O.C(OCC)(=[O:38])C>N1CCCCC1>[CH3:3][S:4]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[O:12])=[CH:7][CH:6]=1)=[O:38]

Participants

6

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 8857Ethyl AcetateHCID 22595687HCID 22595687, compound

Product 1

HCID 30159434-(Methanesulfinyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Conditions

Temperature
100 °C

Procedure

220 mg of 2-[4-(3-chloro-1-thiapropyl)-phenyl]-7-hydroxy-3-(4-hydroxyphenyl)-4-(trifluoromethyl)-2H-1-benzopyran in 2 ml of piperidine is mixed with 42.7 mg of potassium iodide and stirred for 6 hours at 100° C. After cooling, it is poured into water and shaken out three times with ethyl acetate. The combined organic phases are washed twice with water, dried on magnesium sulfate and concentrated by evaporation in a rotary evaporator. The purification of the product is carried out on silica gel with dichloromethane/methanol-9:1. 274 mg of product accumulates.

Workup

  1. temperatureAfter cooling
  2. washThe combined organic phases are washed twice with water
  3. customdried on magnesium sulfate
  4. concentrationconcentrated by evaporation in a rotary evaporator
  5. customThe purification of the product

Sources & evidence

ORD record
ord-72cc06068bd54f58907552f582fca3d1
Source dataset
uspto-grants-2005_01
Patent number
US06844336B2

Reaction notes

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