(Trifluoromethyl)trimethylsilane → HCID 69083891, compound

HRID 1396276Notes

Reaction equation

HRID 1396276 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:17]([CH:18]=[O:19])[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:20]([CH3:22])[CH3:21])[S:14]2)[C@H:10]1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[C:49]([Si](C)(C)C)([F:52])([F:51])[F:50]>C1COCC1>[CH2:1]([O:8][C@@H:9]1[C@@H:17]([C@@H:18]([OH:19])[C:49]([F:52])([F:51])[F:50])[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:20]([CH3:22])[CH3:21])[S:14]2)[C@H:10]1[O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride2×HCID 87687100HCID 87687100, compound

Product 1

HCID 69083891HCID 69083891, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the aldehyde (95) (3.0 g, 7 mmol) (Prepared according to the synthesis of Example 149 step 3) TBAF (1.06 g, 3 mmol) and 4 Å molecular sieves (2.0 g) in THF (60 mL) was stirred for 30 min followed by the addition of CF3SiMe3 (5.8 g, 40 mmol) at −30° C. The mixture was kept overnight at room temperature, additional TBAF (20 g, 63 mmol) was added. After stirred additional 1 hour, the reaction was quenched by brine (40 mL) and extracted with ethyl acetate (3×50 mL). The organic layers combined, washed with brine (3×50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a residue, which was purified by a silica gel column, eluted with 5%-25% ethyl acetate in petroleum ether to afford 110 as a light yellow syrup (1.7 g, 49%). (ES, m/z): [M+H]+ 497.7; 1H NMR (300 MHz, CDCl3) δ 7.31-7.40 (m, 10H), 6.29 (d, J=6.6 Hz, 1H), 4.57-4.78 (m, 4H), 4.30-4.43 (m, 2H), 3.80-4.17 (m, 4H), 3.01 (s, 6H).

Workup

  1. customPrepared
  2. waitThe mixture was kept overnight at room temperature
  3. stirringAfter stirred additional 1 hour
  4. customthe reaction was quenched by brine (40 mL)
  5. extractionextracted with ethyl acetate (3×50 mL)
  6. washwashed with brine (3×50 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto give a residue, which
  10. customwas purified by a silica gel column
  11. washeluted with 5%-25% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-0f47668b32d14f7da4191dda011cdd94
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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