Trifluoroacetic anhydride → HCID 53645319, compound

HRID 1379136Notes

Reaction equation

HRID 1379136 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH2:11][CH2:12][C:13]([OH:15])=O)([CH3:3])[CH3:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O>FC(F)(F)C(O)=O>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:5]=1[S:10][CH2:11][CH2:12][C:13]2=[O:15])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 53831006HCID 53831006, compound

Product 1

HCID 53645319HCID 53645319, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3-(2-Isopropylphenylthio)propanoic acid from Step 1 (6.85 g, 30 mmol) was dissolved in trifluoroacetic acid (20 mL), treated with trifluoroacetic anhydride (12 mL) and stirred at room temperature (64.2 hours). The reaction was concentrated in vacuo, and the residue dissolved in ethyl acetate, extracted with 5% NaOH, washed with brine, dried over MgSO4, and concentrated in vacuo to give a brown oil which was passed through a column of silica gel eluted with 12% ether/hexane to give 8-isopropylthiochroman-4-one as a brown oil (1.05 g, 17%): 1H NMR (CDCl3) 300 MHz 8.01 (d, J=7.0 Hz, 1H) 7.38 (d, J=7.5 Hz, 1H) 7.17 (t, J=7.8 Hz, 1H) 3.19 (m, 3H) 2.96 (m, 2H) 1.25 (d, J=7.0 Hz 6H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate
  3. extractionextracted with 5% NaOH
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give a brown oil which
  8. washeluted with 12% ether/hexane

Sources & evidence

ORD record
ord-6590299801904d8cbf6d6d3acf1b0b17
Source dataset
uspto-grants-1997_09
Patent number
US05670532

Reaction notes

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