Triethylsilane → ethyl 8-ethyl-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 855067Notes

Reaction equation

HRID 855067 reaction equation
O[CH:2]([C:4]1[CH:5]=[C:6]([CH3:23])[CH:7]=[C:8]2[C:13]=1[O:12][CH:11]([C:14]([F:17])([F:16])[F:15])[C:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:9]2)[CH3:3].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:2]([C:4]1[CH:5]=[C:6]([CH3:23])[CH:7]=[C:8]2[C:13]=1[O:12][CH:11]([C:14]([F:15])([F:16])[F:17])[C:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:9]2)[CH3:3]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 69517760ethyl 8-(1-hydroxyethyl)-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 69517395ethyl 8-ethyl-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The ethyl 8-(1-hydroxyethyl)-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Example 6051, Step 1 (0.30 g, 0.91 mmole) was dissolved in trifluoroacetic acid (5 mL). Triethylsilane (0.32 g, 2.73 mmole) was added dropwise to the above solution, which was allowed to stir for 18 hours. The reaction was quenched with saturated sodium bicarbonate (15 mL) and extracted with Et2O (2×20 mL). The combined extracts were washed with brine (20 mL), dried over MgSO4, and filtered. The filtrate was concentrated in vacuo to give a yellow oil which solidified upon standing (0.28 g, 98%): GCMS m/z 314.0 (M+). 1H NMR (CDCl3/400 MHz) 7.66 (s, 1H), 6.98 (s, 1H), 6.85 (s, 1H), 5.70 (q, 1H, J=7.0 Hz), 4.30 (m, 2H), 2.61 (m, 2H), 2.25 (s, 3H), 1.32 (m, 3H), 1.15 (m, 3H).

Workup

  1. customThe reaction was quenched with saturated sodium bicarbonate (15 mL)
  2. extractionextracted with Et2O (2×20 mL)
  3. washThe combined extracts were washed with brine (20 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customto give a yellow oil which

Sources & evidence

ORD record
ord-a627fcccfeae4b9ca575679c97f243b8
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

Loading…