Trifluoroacetic acid → HCID 86718317, compound

HRID 1777082Notes

Reaction equation

HRID 1777082 reaction equation
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[CH3:15][C:16]1[CH:25]=[C:24]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=[CH:23]2)[C:17]=1[CH:26]([C:28]1[S:29][CH:30]=[C:31]([CH3:33])[N:32]=1)O.[OH-].[K+]>ClCCl>[CH3:33][C:31]1[N:32]=[C:28]([CH2:26][C:17]2[C:18]3[C:24]([CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:25][C:16]=2[CH3:15])[S:29][CH:30]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14797Potassium HydroxideHCID 86718316HCID 86718316, compound

Product 1

HCID 86718317HCID 86718317, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylsilane (178 μL, 1.11 mmol) was added slowly to 2 mL of trifluoroacetic acid (TFA) at room temperature. The mixture was cooled to 0° C. and mixed for 30 min. A fresh solution of (2-methylazulen-1-yl)(4-methylthiazol-2-yl)methanol 5 (100 mg, 0.371 mmol) in dichloromethane was then added slowly to the mixture being stirred at 0° C. The reaction was kept at 0° C. for 2 h and then warmed to room temperature. Afterward, the mixture was poured into cold 20% KOH to quench the reaction. The organic layer was extracted into diethyl ether and washed with water and brine, dried with MgSO4 and purified using flash chromatography (ethyl acetate and hexane). The purified material was dried down into a blue solid. Yield: 64.3 mg, 68%. 1H NMR (400 MHz, CDCl3) δ 8.19 (t, J=10.38 Hz, 2H), 7.49 (t, J=9.90 Hz, 1H), 7.21 (s, 1H), 7.17-7.10 (m, 2H), 6.60 (s, 1H), 4.68 (s, 2H), 2.60 (s, 3H), 2.42 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 171.8, 152.1, 149.0, 140.1, 137.0, 135.8, 134.4, 131.5, 123.2, 122.7, 117.8, 113.1, 29.3, 17.0, 15.0. HRMS (ES) calcd. MH+ [C16H16NS]+ 254.0925. found 254.0990.

Workup

  1. additionmixed for 30 min
  2. temperaturewarmed to room temperature
  3. customto quench
  4. customthe reaction
  5. extractionThe organic layer was extracted into diethyl ether
  6. washwashed with water and brine
  7. dry with materialdried with MgSO4
  8. custompurified
  9. customThe purified material was dried down into a blue solid

Sources & evidence

ORD record
ord-6bdc8c1e33be4198b0c7193c97972a38
Source dataset
uspto-grants-2016_02
Patent number
US09266847B2

Reaction notes

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