Triethylsilane → ethyl 7-(4-methylbenzyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854882Notes

Reaction equation

HRID 854882 reaction equation
[CH3:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:14]([C:18]([F:21])([F:20])[F:19])[O:15]3)=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.[SiH](CC)(CC)CC>C(O)(C(F)(F)F)=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:14]([C:18]([F:21])([F:20])[F:19])[O:15]3)=[CH:10][CH:9]=2)=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 69519424ethyl 7-(4-methylbenzoyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 69517327ethyl 7-(4-methylbenzyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The ester from Step 1 was dissolved in TFA (18 mL). Et3SiH was added dropwise at room temperature. The reaction was stirred at room temperature overnight. The reaction was quenched with NaHCO3 and extracted with ether. The organic layer was dried over MgSO4. The filtrate was concentracted to give yellow oil, which was purified by Biotage with 3-5% EtOAc in hexane to give clear oil quantity: LCMS m/z 377.15 (M+H). 1H NMR (CDCl3/400 MHz) 7.68 (s, 1H), 7.08 (m, 4H), 6.79 (d, 1H, J=6.4 Hz), 5.68 (q, 1H, J=7.2 Hz), 4.29 (m, 2H), 3.89 (s, 2H), 2.31 (s, 3H), 1.35 (t, 3H, J=7.2 Hz).

Workup

  1. customThe reaction was quenched with NaHCO3
  2. extractionextracted with ether
  3. dry with materialThe organic layer was dried over MgSO4
  4. customto give yellow oil, which
  5. customwas purified by Biotage with 3-5% EtOAc in hexane
  6. customto give clear oil quantity

Sources & evidence

ORD record
ord-e53e13cc64914efbbb1312f9c6cb348b
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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