Methanol → HCID 67458030, compound

HRID 554571Notes

Reaction equation

HRID 554571 reaction equation
C([SiH](CC)CC)C.[Br:8][C:9]1[CH:10]=[C:11]([CH:18]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH3:27])=[CH:22][CH:21]=2)O)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][CH3:17].CO.O>C(Cl)Cl>[Br:8][C:9]1[CH:10]=[C:11]([CH2:18][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH3:27])=[CH:22][CH:21]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 12052TriethylsilaneHCID 67459476HCID 67459476, compound

Product 1

HCID 67458030HCID 67458030, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylsilane (2.7 mL, 16.9 mmol) and a boron trifluoride-diethyl ether complex (1.2 mL, 9.47 mmol) were added to a solution of (3-bromo-4-ethoxyphenyl)-(4-ethylphenyl)methanol (2.83 g, 8.44 mmol) in methylene chloride (20 mL) at 0° C. and the mixture was stirred for three hours. Methanol (50%)-water (4 mL) was added to the reaction mixture and the resulting mixture was extracted with methylene chloride. The extract was washed with a saturated sodium chloride aqueous solution, and then dried over magnesium sulfate. The residue obtained by distilling the solvent under reduced pressure was purified by silica gel column chromatography {developing solution=n-hexane to n-hexane-ethyl acetate [4% (v/v)]} to obtain the title compound (2.69 g, 100%).

Workup

  1. extractionthe resulting mixture was extracted with methylene chloride
  2. washThe extract was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. customThe residue obtained
  5. distillationby distilling the solvent under reduced pressure
  6. customwas purified by silica gel column chromatography {

Sources & evidence

ORD record
ord-a2cbea689add433ab7a51d9fffafa38b
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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