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

HRID 855063Notes

Reaction equation

HRID 855063 reaction equation
O[CH:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:3]1[CH:4]=[C:5]([CH3:22])[CH:6]=[C:7]2[C:12]=1[O:11][CH:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8]2.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:2]([C:3]1[CH:4]=[C:5]([CH3:22])[CH:6]=[C:7]2[C:12]=1[O:11][CH:10]([C:13]([F:16])([F:14])[F:15])[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8]2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 69517053ethyl 8-[hydroxy(phenyl)methyl]-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 69517454ethyl 8-benzyl-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The ethyl 8-[hydroxy(phenyl)methyl]-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate (0.28 g, 0.70 mmole) was dissolved in trifluoroacetic acid (5 mL). Triethylsilane (0.24 g, 2.10 mmole) was added dropwise to above solution, which was allowed to stir for 18 hours. The reaction was quenched with saturated sodium bicarbonate (15 mL) and extracted with EtOAc (2×20 mL). The combined extracts were washed with brine (20 mL), dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil, which solidified upon standing (0.3 g, 98%): GCMS m/z 376.0 (M+). 1H NMR (CDCl3/400 MHz) 7.67 (s, 1H), 7.25 (m, 3H), 7.20 (m, 2H), 6.93 (s, 1H), 6.89 (s, 1H), 5.70 (q, 1H, J=7.0 Hz), 4.29 (m, 2H), 3.94 (m, 2H), 2.22 (s, 3H), 1.32 (m, 3H).

Workup

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

Sources & evidence

ORD record
ord-e4564183b8c7414b81371919d28bd118
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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