Methanol → HCID 10515154, compound

HRID 2085572Notes

Reaction equation

HRID 2085572 reaction equation
[C:1]([C:4]1[C:12]2[O:11][CH2:10][C:9]([CH3:14])([CH3:13])[C:8]=2[CH:7]=[C:6]([Br:15])[CH:5]=1)(=O)[CH3:2].C([SiH](CC)CC)C.CO.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O.O>[Br:15][C:6]1[CH:5]=[C:4]([CH2:1][CH3:2])[C:12]2[O:11][CH2:10][C:9]([CH3:13])([CH3:14])[C:8]=2[CH:7]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 22731331HCID 22731331, compound2×

Product 1

HCID 10515154HCID 10515154, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 7-acetyl-5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran (Intermediate 13, 0.125 g, 0.5 mmol) in 3 mL of trifluoroacetic acid was treated with triethyl silane (0.9 mL, 11.3 mmol) and the resulting clear, colorless solution was heated at 55° C. for 2 h. The reaction mixture was cooled, treated with 6 mL each of methanol and water, neutralized cautiously with saturated sodium bicarbonate solution and extracted with hexanes. The organic extract was dried over anhydrous sodium sulfate, filtered and evaporated to an oil. Flash column chromatography using 2% ethyl acetate in hexane as the eluent afforded the title compound (0.11 g, 93%) as an oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with hexanes
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated to an oil

Sources & evidence

ORD record
ord-9a143f626f1d4f9fa067e2e44fdc41a7
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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