Chloroacetone → HCID 66764935, compound

HRID 1466834Notes

Reaction equation

HRID 1466834 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([S:14][Si](C(C)C)(C(C)C)C(C)C)[CH:7]=1)[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl[CH2:45][C:46](=[O:48])[CH3:47]>C1COCC1>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([S:14][CH2:45][C:46](=[O:48])[CH3:47])[CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 2724141Tetrabutylammonium FluorideHCID 66764878HCID 66764878, compound

Product 1

HCID 66764935HCID 66764935, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(4-Methoxy-3-triisopropylsilanylsulfanyl-phenyl)-acetic acid ethyl ester (2.5 g, 6.53 mmol) was dissolved in THF (40 mL) and cooled to 0° C. Tetrabutylammonium fluoride (6.6 mL, 1.0M in THF, 6.6 mmol) was added and the reaction stirred for 15 minutes, after which time analytical TLC indicated complete reaction. Chloroacetone (0.520 mL, 6.53 mmol) was then added and the reaction was allowed to warm to room temperature. When analytical TLC indicated the reaction was complete, it was submitted to standard workup procedures then purified via silica gel chromatography to yield the title compound.

Workup

  1. customreaction
  2. temperatureto warm to room temperature
  3. customthen purified via silica gel chromatography

Sources & evidence

ORD record
ord-48fb757a996242759855193cab04c092
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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