Trifluoroacetic anhydride → HCID 53645319, compound

HRID 1419079Notes

Reaction equation

HRID 1419079 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 vacua, and the residue dissolved in ethyl acetate, extracted with 5% NaOH, washed with brine, dried over MgSO4, and concentrated in vacua 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 vacua
  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 vacua
  7. customto give a brown oil which
  8. washeluted with 12% ether/hexane

Sources & evidence

ORD record
ord-b19b9bdb84a74b32bfb87b514f8d6563
Source dataset
uspto-grants-1999_03
Patent number
US05886016

Reaction notes

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