Trifluoroacetic anhydride → HCID 849527, compound

HRID 1379139Notes

Reaction equation

HRID 1379139 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9][CH2:10][CH2:11][C:12]([OH:14])=O)[CH:6]=[CH:7][CH:8]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.CCOCC.CCCCCC>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6]([C:12](=[O:14])[CH2:11][CH2:10][S:9]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 5314229HCID 5314229, compoundHCID 21584099Diethylether hexane

Product 1

HCID 849527HCID 849527, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The acid from Step 1 (2.55 g, 12 mmol) was dissolved in trifluoroacetic acid (10 mL), treated with trifluoroacetic anhydride (5 mL) and stirred at room temperature (10 minutes). The reaction was poured into 10% Na2 CO3 (60 mL), extracted with ether, washed with brine, dried over MgSO4, and concentrated in vacuo to give a red oil which was passed through a column of silica gel with 50% ether/hexane to give 7-methoxythiochroman-4-one as an orange solid (1.18 g, 51%): mp 49°-51° C.; 1H NMR (CDCl3) 300 MHz 8.06 (d, J=8.9 Hz, 1H) 6.72 (m, 2H) 3.83 (s, 3H) 3.20 (m, 2H) 2.95 (m, 2H). Mass spectrum: M+H=195.

Workup

  1. extractionextracted with ether
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto give a red oil which

Sources & evidence

ORD record
ord-76b1ed8bfde64672a620108049858dbb
Source dataset
uspto-grants-1997_09
Patent number
US05670532

Reaction notes

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