Trifluoroacetic acid → 116174-33-5

HRID 1246389Notes

Reaction equation

HRID 1246389 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:5][CH:4]=1.FC(F)(F)C(O)=O.[H-].C([SiH](CC)CC)C>>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 20637154-[4-(methylthio)phenyl]-4-oxobutanoic acidHCID 131724811HCID 131724811, compound

Product 1

HCID 21916663116174-33-5

Procedure

A solution of the acid obtained in Step A (19.8 g, 88.1 mmol) in trifluoroacetic acid (68 ml, 881 mmol) is brought to 0° C. and then triethylsilane hydride (35.2 ml, 220 mmol) is added dropwise using a dropping funnel. Stirring is carried out at ambient temperature for 17 hours. After hydrolysis, the white precipitate formed is filtered off, rinsed with water and with cyclohexane and is then purified by chromatography on silica gel (eluant: acetone/toluene/cyclohexane 30/50/20) to yield the title compound.

Workup

  1. customis brought to 0° C.
  2. customAfter hydrolysis
  3. customthe white precipitate formed
  4. filtrationis filtered off
  5. washrinsed with water and with cyclohexane
  6. customis then purified by chromatography on silica gel (eluant: acetone/toluene/cyclohexane 30/50/20)

Sources & evidence

ORD record
ord-285789beb29c4c7498f7fb62c5725631
Source dataset
uspto-grants-2006_10
Patent number
US07126012B2

Reaction notes

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