Triethylsilane → 6-Bromo-8-ethyl-2,2,4,4-tetramethyl chroman

HRID 844677Notes

Reaction equation

HRID 844677 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([Br:18])[CH:7]=[C:8]2[C:13]=1[O:12][C:11]([CH3:15])([CH3:14])[CH2:10][C:9]2([CH3:17])[CH3:16])(=O)[CH3:2].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Br:18][C:6]1[CH:7]=[C:8]2[C:13](=[C:4]([CH2:1][CH3:2])[CH:5]=1)[O:12][C:11]([CH3:15])([CH3:14])[CH2:10][C:9]2([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 211072398-Acetyl-6-bromo-2,2,4,4-tetramethyl chroman2×

Product 1

HCID 695485316-Bromo-8-ethyl-2,2,4,4-tetramethyl chroman

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A stirred, cooled (ice bath) solution of 8-acetyl-6-bromo-2,2,4,4-tetramethyl chroman (Intermediate 45, 0.95 g, 3.1 mmol) in trifluoroacetic acid (10 mL) was treated with triethylsilane (10 mL) and the resulting reaction mixture was allowed to warm to ambient temperature and stirred overnight. The volatiles were distilled off in vacuo and the residue was diluted with water and extracted with hexane (×2). The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to an oil which was subjected to flash column chromatography over silica gel (230-400 mesh) using hexane as the eluent to afford the title compound as a clear oil, contaminated with a small amount to triethylsilane (0.51 g, 56%).

Workup

  1. customthe resulting reaction mixture
  2. distillationThe volatiles were distilled off in vacuo
  3. additionthe residue was diluted with water
  4. extractionextracted with hexane (×2)
  5. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to an oil which

Sources & evidence

ORD record
ord-be67bb8eb88c43a7a02c90e6c5fcf07d
Source dataset
uspto-grants-2002_04
Patent number
US06380256B1

Reaction notes

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