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

HRID 1861378Notes

Reaction equation

HRID 1861378 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([Br:54])[CH:7]=[C:8]2[C:13]=1[O:12][C:11]([CH:24]1C(C(C)C)CCC(C)C1)([CH:14]1C(C(C)C)CCC(C)C1)[CH2:10][C:9]2([CH:44]1C(C(C)C)CCC(C)C1)[CH:34]1C(C(C)C)CCC(C)C1)(=O)[CH3:2].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Br:54][C:6]1[CH:7]=[C:8]2[C:13](=[C:4]([CH2:1][CH3:2])[CH:5]=1)[O:12][C:11]([CH3:24])([CH3:14])[CH2:10][C:9]2([CH3:34])[CH3:44]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 70025477HCID 70025477, compound2×

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-tetramenthyl 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-93c4670f3d7f4c3591c9e3398ea363f1
Source dataset
uspto-grants-2003_03
Patent number
US06531599B2

Reaction notes

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