1,1-Dimethylethyl 2-acetyl-3-oxo-4-(phenylthio)butanoate → 1-(Phenylthio)pentane-2,4-dione

HRID 1013102Notes

Reaction equation

HRID 1013102 reaction equation
[C:1]([CH:4]([C:12](=[O:21])[CH2:13][S:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)C(OC(C)(C)C)=O)(=[O:3])[CH3:2]>C(O)(C(F)(F)F)=O>[C:15]1([S:14][CH2:13][C:12](=[O:21])[CH2:4][C:1](=[O:3])[CH3:2])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 1

HCID 574477431,1-Dimethylethyl 2-acetyl-3-oxo-4-(phenylthio)butanoate

Product 1

HCID 125296471-(Phenylthio)pentane-2,4-dioneYield 69%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-(Phenyltlhio)pentane-2,4-dione Stir 1,1-dimethylethyl 2-acetyl-3-oxo-4-(phenylthio)butanoate (1.11 g, 3.60 mmol) in TFA (3 mL) for 20 h at RT. Quench with water (10 mL), and extract using diethyl ether (10 mL). Wash organic layer with water (3×10 mL), dry (MgSO4), concentrate and purify (silica gel chromatography, eluting with 100:0 to 80:20 2-methylpentane:EtOAc) to give the title compound as an orange oil (513 mg, 69%).

Workup

  1. customQuench with water (10 mL)
  2. extractionextract
  3. dry with materialWash organic layer with water (3×10 mL), dry (MgSO4)
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 100:0 to 80:20 2-methylpentane:EtOAc)

Sources & evidence

ORD record
ord-6c3128bb8e684b8d97be976c9d6fb1b3
Source dataset
uspto-grants-2011_07
Patent number
US07981882B2

Reaction notes

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